Xiaopeng Yin The Wulff Group Michigan State University 6/6/2014. Career Summary. Eric N. Jacobsen
|
|
|
- Arron Mosley
- 6 years ago
- Views:
Transcription
1 Xiaopeng Yin The Wulff Group Michigan State University 6/6/2014 Career Summary Eric N. Jacobsen
2 About Eric N. Jacobsen PERSONAL Born February 22, 1960, New York, N.Y. Married to Virginia Estevez on May 17, Three daughters (Adriana, Isabel, and Emilia) EDUCATION : New York University, New York, New York. Degree awarded: B.S. in Chemistry Research advisor ( ): Professor Yorke E. Rhodes : University of California, Berkeley, California. Degree awarded: Ph.D. Research advisor: Professor Robert G. Bergman : National Institutes of Health Postdoctoral Fellow Massachusetts Institute of Technology, Cambridge, Massachusetts. Research advisor: Professor K. Barry Sharpless Development of the osmium-catalyzed asymmetric dihydroxylation reaction. EMPLOYMENT : University of Illinois at Urbana-Champaign Assistant Professor (June 1988-September 1991) Associate Professor (September 1991-June 1993) 1993-present: Harvard University Professor (July 1993-June 2001) Sheldon Emery Professor of Chemistry (July 2001-present)
3 Group Members Present Graduate Students: 9 Postdocs: 11 Past Ph.D Students: 37 Postdocs: 80 Mini Group Reunion in summer 2011
4 Publications research articles (70 JACS, 27 Angew, 2 Science, 1 Nature, 1 Natrue Chem.) 23 reviews 16 patents
5 Citations Sum of Times Cited without selfcitations : Citing Articles without selfcitations: Average Citations per Item: Top 3 cited research articles: 1. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. "Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by (salen)manganese Complexes," J. Am. Chem. Soc. 1990, 112, (1243, 50/y) 2. Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.; Jacobsen, E.N. "Asymmetric Catalysis with Water: Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic Hydrolysis," Science 1997, 277, (900, 50/y) 3. Schaus, S. E.; Brandes, B. D; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. "Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)cobalt(iii)-complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols," J. Am. Chem. Soc. 2002, 124, (616, 47/y)
6 Catalysts* Salen Complexes H-bond Donors (Schiff Base)Cr Complex Other * Summarized from 151 Independent research papers in selected journals
7 Metal of Salen Complexes * Co Mn Cr Al Cu * Summarized from 151 Independent research papers in selected journals
8 H-bond Donors* thiourea urea guanidinium * Summarized from 151 Independent research papers in selected journals
9 Reaction* Epoxidation Epoxides Ring Opening Aziridinization Conjugate Addition Cycloadditions C=C functionalization C=O functionalization C=N functionalization C=O α-functionalization Mechanism Study Catalyst Study other * Summarized from 151 Independent research papers in selected journals Total Synthesis
10 Jacobsen Asymmetric Epoxidation of Olefins 9 substrates, 36-75% yield, 20-93% ee, only cis-alkene gave good results 6 cis-alkene substrates, 63-96% yield, 89-98% ee Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113,
11 Preparation of Catalyst Palucki, M.; Finney, N.S.; Pospisil, P.J.; Güler, M.L.; Ishida, T.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120,
12 Side on Mechanism Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, Palucki, M.; Finney, N.S.; Pospisil, P.J.; Güler, M.L.; Ishida, T.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120,
13 Substrate limitation Terminal alkenes Properties favoring high enantioselectivity mcpba, -78 C, 30 min, Catalyst 3 88% yield, 86% ee Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martínez, L. E. Tetrahedron 1994, 50, Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116,
14 Substrate limitation Trisubstituted alkenes 6 substrates, 61-97% yield, 86-95% ee, Tetrasubstituted alkenes Catalyst 2, 84% yield, 96% ee Catalyst 2, 81% yield, 97% ee Catalyst 3, 45% yield, 65% ee Catalyst 3, 37% yield, 35% ee Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, Brandes, B. D.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36,
15 Trans Epoxides Cis-enynes and cis-dienes 65% yield, t/c = 5:1 98% ee 58% yield, t/c = 7:1 83% ee 81% yield, t/c = 9:1 87% ee Chiral Quaternary Ammonium Salts additives Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, Chang, S.; Lee, N. H.; Jacobsen, E. N. J. Org. Chem. 1993, 58, Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116,
16 Ring Opening of Epoxides Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117,
17 Kinetic Resolution with TMSN 3 Larrow, J.F.; Schaus, S.E.; Jacobsen, E.N. J. Am. Chem. Soc. 1996, 118,
18 Hydrolytic Kinetic Resolution (HKR) Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.; Jacobsen, E.N. Science 1997, 277,
19 Mechanism and Improvement Method A: X = OAc Method B: X = OTs Nielsen, L. C. P.; Stevenson, C. P.; Blackmond, D.G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, Nielsen, L. P. C.; Zuend, S. J.; Ford, D. D.; Jacobsen, E. N. J. Org. Chem., 2012, 77,
20 Mechanism and Improvement Ready, J. R.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2002, 41, Breinbauer, R.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2000, 39,
21 Stereochemical Communication Between Catalysts Ford, D. D.; Nielsen, L. P. C.; Zuend, S. J.; Musgrave, C. B.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135,
22 Phenolytic Kinetic Resolution (PKR) Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121,
23 Asymmetric Alkene Aziridination Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117,
24 Enantioselective Michael Additions
25 Enantioselective Michael Additions Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125,
26 Enantioselective Michael Additions Cooperative Dual Catalysis Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126,
27 Enantioselective Michael Additions Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125,
28 Enantioselective Michael Additions 9 examples, 76-93% yield, 75-96% ee, 8 examples, 70-90% yield, 88-95% ee, 7 examples, 72-97% yield, 61-94% ee, Taylor, M. S.; Zalatan, D. N.; Lerchner, A. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127,
29 Asymmetric Hetero-Diels-Alder Reactions Schaus, S.E.; Brånalt, J.E.; Jacobsen, E.N. J. Org. Chem. 1998, 63,
30 Asymmetric Hetero-Diels-Alder Reactions 14 examples, 50-97% yield, 81-99% ee, Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. "Angew. Chem. Int. Ed. 1999, 38,
31 Total Synthesis of FR Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2000, 122, Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123,
32 Total Synthesis of (+)-Ambruticin Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123,
33 Synthesis of the Catalyst Schaus, S.E.; Brånalt, J.E.; Jacobsen, E.N. J. Org. Chem. 1998, 63,
34 Inverse Electron Demand Hetero-Diels Alder Reactions Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2002, 41, Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5,
35 Quinone Diels Alder Reactions and Application Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2005, 44, Boezio, A. A.; Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2005, 44,
36 Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, Ruck, R. T.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2003, 42, Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, Hetero-Ene Reactions 18 examples, 50-98% yield, 70-96% ee 6 examples, 47-90% yield, 87-93% ee 42% yield, 93% ee, dr>30:1
37 Asymmetric Strecker Reaction R= Ar, 7 examples, % yield, 79-95% ee R= Alkyl, 2 examples, % yield, 37-57% ee M = Al(III)Cl Sigman, M.S.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120, Sigman, M.S.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120,
38 Thiourea Catalyst 6 examples, % yield, 70-91% ee Sigman, M.S.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120,
39 Mode of Activation Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124,
40 Mode of Activation Zuend, S. J.; Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. Nature 2009, 461, Zuend, S. J., Jacobsen, E. N. J. Am. Chem. Soc. 2009, 131,
41 Activation of Imines Mannich Reactions R= Ar, 14 examples, % yield, 86-98% ee Hydrophosphonylation 18 examples, % yield, 81-99% ee Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126,
42 Activation of Imines and Ketones Povarov Reactions Cyanosilylation of Ketones 18 examples, % yield, 86-98% ee Xu, H.; Zuend, S. J.; Woll, M. P.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, Fuerst, D. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127,
43 H-bonding Anion Stabilization Acyl-Pictet-Spengler Reactions Pictet-Spengler-Type Cyclizations 7 examples, % yield, 85-95% ee 15 examples, % yield, 81-99% ee Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, Brown, A. R.; Uyeda, C.; Raheem, I. T.; Thiara, P. V.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129,
44 H-bonding Anion Stabilization Raheem, I. T.; Thiara, P. V.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129,
45 H-bonding Anion Stabilization Additions to Oxocarbenium Ions 6 examples, % yield, 74-90% ee Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130,
46 H-bonding Anion Stabilization Cationic Polycyclizations Iodolactonization 7 examples, % yield, 89-94% ee 9 examples, % yield, 48-96% ee Knowles, R. R.; Lin, S.: Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, Veitch, G. E.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2010, 49,
47 H-bonding Anion Stabilization α-alkylation of Aldehydes [5+2] Pyrylium Cycloadditions 9 examples, % yield, 85-94% ee Brown, A. R.; Kuo, H.-S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, Burns, N. Z.; Witten, M. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133,
48 H-bonding TS Stabilization Claisen Rearrangements Guanidinium Catalysts Cope-Type Hydroamination Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, Brown, A. R.; Uyeda, C.; Brotherton, C. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135,
49
The Career of Tristan H. Lambert
The Career of Tristan H. Lambert Jian Rong( 荣健 ) Hu Group Meeting Apr 11, 2016 Tristan H. Lambert: Biographical Notes Professional experience 2011-present: Associate Professor, Columbia University 2006-2011:
Career Review of Dean Toste I. 2015/9/9 Zhi Ren
Career Review of Dean Toste I 2015/9/9 Zhi Ren Introduction F. Dean Toste, now in UC Berkeley Career: Full Professor since 2009-now Associate Professor 2006-2009 Assistant Professor 2002-2006 Faculty Scientist
Bifunctional Asymmetric Catalysts: Design and Applications. Junqi Li CHEM Sep 2010
Bifunctional Asymmetric Catalysts: Design and Applications Junqi Li CHEM 535 27 Sep 2010 Enzyme Catalysis vs Small-Molecule Catalysis Bronsted acid Lewis acid Lewis acid Bronsted base Activation of both
The Hydrolytic Kinetic Resolution Jacobsen s Catalyst
The Hydrolytic Kinetic Resolution Jacobsen s Catalyst CHEM 373 Advanced rganic Lab Kenyon College Yutan Getzler The Hydrolytic Kinetic Resolution Jacobsen s Catalyst by Yutan D. Y L. Getzler is licensed
Asymmetric Catalysis by Lewis Acids and Amines
Asymmetric Catalysis by Lewis Acids and Amines Asymmetric Lewis acid catalysis - Chiral (bisooxazoline) copper (II) complexes - Monodentate Lewis acids: the formyl -bond Amine catalysed reactions Asymmetric
Chiral Brønsted Acid Catalysis
another. 1 One interesting aspect of chiral Brønsted acid catalysis is that the single s orbital of hydrogen Chiral Brønsted Acid Catalysis Reported by Matthew T. Burk December 3, 2007 INTRODUCTION The
Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions
Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions 1. Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, ASAP. 2. Storer, R. L.; Carrera, D. E.;
Advanced Organic Chemistry
D. A. Evans, G. Lalic Question of the day: Chemistry 530A TBS Me 2 C Me toluene, 130 C 70% TBS C 2 Me H H Advanced rganic Chemistry Me Lecture 16 Cycloaddition Reactions Diels _ Alder Reaction Photochemical
Catalytic Asymmetric Total Syntheses of Quinine and Quinidine
Catalytic Asymmetric Total Syntheses of Quinine and Quinidine 8 7 9 2 1 3 4 6 5 7 9 8 2 1 3 4 6 5 Quinine Zhensheng Ding Quinidine January 22 2004 Chinese ew Year Day 1. Jacobsen, E.,. J. Am. Chem. Soc.
Chiral Brønsted Acid Catalysis
Chiral Brønsted Acid Catalysis Aryl Aryl Aryl Aryl S CF 3 2 P Fe CF 3 CF 3 2 Jack Liu ov. 16, 2004 CF 3 Introduction Chiral Brønsted acid catalysis in nature: enzymes and peptides Chiral Brønsted acid
Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet Spengler Reaction of Indolyl Dihydropyridines
Literature Report V Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet Spengler Reaction of Indolyl Dihydropyridines Reporter Checker Date : Xiao-Yong Zhai : Xin-Wei Wang : 2018-04-02 You,
Silica-Supported Cationic Gold(I) Complexes as Heterogeneous Catalysts for Regio- and Enantioselective Lactonization Reactions
Silica-Supported Cationic Gold(I) Complexes as Heterogeneous Catalysts for Regio- and Enantioselective Lactonization Reactions Xing-Zhong Shu, Son C. Nguyen,Ying He, Fadekemi Oba, Qiao Zhang, Christian
Literature Report. Catalytic Enantioselective Synthesis of Isoindolinones through a Biomimetic Approach. : Zhong Yan : Ji Zhou :
Literature Report Catalytic Enantioselective Synthesis of Isoindolinones through a Biomimetic Approach Reporter Checker Date : Zhong Yan : Ji Zhou : 2017-12-22 Min, C.; Lin, Y.; Seidel, D. Angew. Chem.
CATALYSIS MULTICATALYST SYSTEM IN ASYMMETRIC. Wiley. Department of Chemistry
MULTICATALYST SYSTEM IN ASYMMETRIC CATALYSIS JIAN ZHOU Shanghai Key Laboratory of Green Chemistry and Chemical Processes Department of Chemistry East China Normal University Shanghai, China Wiley Preface
Povarov Reaction. Zain Yousaf 10/22/2013 University of Illinois at Urbana-Champaign
Povarov Reaction Zain Yousaf 10/22/2013 University of Illinois at Urbana-Champaign Contents Introduction Chiral Lewis Acids Bronsted Acid Lanthanide complexes L-ramipril acid derived Sulfonamide Urea Derivative
Hao Xu, Ph.D. Current Research Topics Discovery of iron-catalyzed nitrogen atom transfer reactions for stereoselective olefin functionalization.
Hao Xu, Ph.D. Curriculum Vitae Georgia State University Tel: (404) 413-5553 Department of Chemistry Petit Science Center 319 Fax: (404) 413-5505 100 Piedmont Ave. SE http://sites.gsu.edu/hxu Atlanta, GA
The synthesis of molecules containing quaternary stereogenic centers via the intramolecular asymmetric Heck reaction. Eric Gillis 4/19/07
The synthesis of molecules containing quaternary stereogenic centers via the intramolecular asymmetric Heck reaction Eric Gillis 4/19/07 Quaternary stereocenters in complex small molecules Retrosynthetic
Dr. P. Wipf Chem /10/2007
I. Basic Principles I-N. Epoxides 1. High-Valent TM(d0) Epoxidations Mo, V, W (H 2 WO 4 ), Ti, Al serve as catalysts with t-buo 2 H or other peroxides as stoichiometric oxidants. Toluene is a frequent
4. T. Ooi, M. Kameda, M. Taniguchi, and K. Maruoka, Development of Highly
Ph. D. 二二Pʰ.D. organocatalyst (Maruoka Catalyst ) LFA-1 BIRT-377 ACE 二二 主要発表論文 総説および著書二二8. T. Ooi Y. Uematsu, and K. Maruoka, Asymmetric Strecker Reaction of Aldimines Using Aqueous Potassium Cyanide by
II. Special Topics IIA. Enolate Chemistry & the Aldol Reaction
P. Wipf - Chem 2320 1 3/20/2006 II. Special Topics IIA. Enolate Chemistry & the Aldol Reaction Boger Notes: p. 147-206 (Chapter VIII) Carey/Sundberg: B p. 57-95 (Chapter B 2.1) Problem of the Day: Wang,
Shi Asymmetric Epoxidation
Shi Asymmetric Epoxidation Chiral dioxirane strategy: R 3 + 1 xone, ph 10.5, K 2 C 3, H 2, C R 3 formed in situ catalyst (10-20 mol%) is prepared from D-fructose, and its enantiomer from L-sorbose oxone,
N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Enantioselective Remote Functionalizations
Angew. Chem. Int. Ed. 2017, 10.1002. 1 N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Enantioselective Remote Functionalizations Reporter: En Li Supervisor: Prof. Yong
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid Shiqing Xu, Akimichi Oda, Thomas Bobinski, Haijun Li, Yohei Matsueda, and Ei-ichi Negishi Angew. Chem. Int. Ed. 2015,
Enantioselective Borylations. David Kornfilt Denmark Group Meeting Sept. 14 th 2010
Enantioselective Borylations David Kornfilt Denmark Group Meeting Sept. 14 th 2010 30.000-foot View Enantioenriched Organoboranes What to do with them Crudden C. M. et. al., Eur. J. Org. Chem. 2003, 46
Regioselective Reductive Cross-Coupling Reaction
Lit. Seminar. 2010. 6.16 Shinsuke Mouri (D3) Regioselective Reductive Cross-Coupling Reaction Glenn C. Micalizio obtained a Ph.D. at the University of Michigan in 2001 under the supervision of Professor
Functionalization of C(sp 3 ) H Bonds Using a Transient Directing Group
Literature eport Functionalization of C(sp 3 ) Bonds Using a Transient Directing Group eporter: Mu-Wang Chen Checker: Yue Ji Date: 2016-04-05 Yu, J.-Q. et al. Science 2016, 351, 252-256. Scripps esearch
Asymmetric Catalysis by Chiral Hydrogen-Bond Donors
Asymmetric Catalysis by Chiral Hydrogen-Bond Donors Angew. Chem. Int. Ed., 2006, 45, 1520~1543 Mark S. Taylor and Eric N. Jacobsen* Current Literature Presentation Zhenglai Fang Wipf s Group at Pitt Zhenglai
Asymmetric Hydrogen-Bond catalysis
Asymmetric Hydrogen-Bond catalysis Topic review Joséphine Cinqualbre Group of Prof. P. Renaud Universität Bern 30.10.2014 Table of contents Introduction Double H-bond catalysts Thioureas Pioneer work Monofunctional
Literature Report 2. Divergent Asymmetric Total Synthesis of Mulinane Diterpenoids. Date :
Literature Report 2 Divergent Asymmetric Total Synthesis of Mulinane Diterpenoids Reporter : Zhou-Hao Zhu Checker : Xiao-Yong Zhai Date : 2018-04-23 Liu, Y.-T.; Li, L.-P.; Xie, J.-H.*; Zhou, Q.-L. Angew.
Hydrogen-Mediated C-C Bond Formation
EPFL - ISIC - LSPN Hydrogen-Mediated C-C Bond Formation History and selected examples The Research of Prof. Michael Krische (University of Texas at Austin) LSPN Group Seminar Mathias Mamboury Table of
Diels Alder cycloaddition
I p1.1.1 The Diels Alder Cycloaddition Reaction in the Context of Domino Processes J. G. West and E. J. Sorensen The Diels Alder cycloaddition has been a key component in innumerable, creative domino transformations
C h a p t e r 1. Enantioselective LUMO-Lowering Organocatalysis. The presentation of the Nobel Prize in 2001 to William S. Knowles, Ryoji Noyori,
1 C h a p t e r 1 Enantioselective LUM-Lowering rganocatalysis. I. Introduction. The presentation of the obel Prize in 2001 to William S. Knowles, Ryoji oyori, and K. Barry Sharpless recognized the influence
O + k 2. H(D) Ar. MeO H(D) rate-determining. step?
ame: CEM 633: Advanced rganic Chem: ysical Problem Set 6 (Due Thurs, 12/8/16) Please do not look up references until after you turn in the problem set unless otherwise noted. For the following problems,
Anti-Markovnikov Olefin Functionalization
Anti-Markovnikov Olefin Functionalization ~Prof. Robert H. Grubbs Work~ 4 th Literature Seminar July 5, 2014 Soichi Ito (D1) Contents 1. Introduction Flow of Prof. Grubbs Research Markovnikov s Rule Wacker
Epoxidation with Peroxy Acids
Epoxidation with Peroxy Acids RC 3 R C more reactive more likely Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M.; Rastelli, A. J. rg. Chem. 2000, 65, 2030. Singleton, D. A.; Merrigan, S. R.; Liu, J.; ouk,
Stereodivergent Catalysis. Aragorn Laverny SED Group Meeting July
Stereodivergent Catalysis Aragorn Laverny SED Group Meeting July 31 2018 1 Stereodivergent Catalysis In the context of asymmetric synthesis, a stereodivergent process is one that allows access to any given
Experiment #3: Asymmetric Synthesis Use of a Chiral Manganese Catalyst for the Enantioselective Epoxidation of Alkenes
Experiment #3: Asymmetric Synthesis Use of a Chiral Manganese Catalyst for the Enantioselective Epoxidation of Alkenes INTRODUCTION Chemists have discovered and developed many elegant and synthetically
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity Reporter: Cong Liu Checker: Hong-Qiang Shen Date: 2017/02/27
C H Activated Trifluoromethylation
Literature report C H Activated Trifluoromethylation Reporter:Yan Fang Superior:Prof. Yong Huang Jun. 17 th 2013 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation
Catalytic alkylation of remote C H bonds enabled by proton-coupled electron transfer
Catalytic alkylation of remote C bonds enabled by proton-coupled electron transfer Reporter: Ji Zhou Checker: Shubo u Date: 2016/11/14 Choi, G. J.; Zhu, Q.-L.; Miller, D. C.; Gu, C. J.; Knowles, R. R.
Non-Enzymatic Enantioselective Polyene Cyclizations. Adam Hill Chem 535 May, 2 nd 2013
Non-Enzymatic Enantioselective Polyene Cyclizations Adam Hill Chem 535 May, 2 nd 2013 Enantioselective Polyene Cyclization (?) General Method to Rapidly Build Molecular Complexity (+) Exquisite Stereo-
Story Behind the Well-Developed Chiral Lewis Acid in Asymmetric Diels-Alder reaction
Story Behind the Well-Developed Chiral Lewis Acid in Asymmetric Diels-Alder reaction Reporter: Zhang Sulei Supervisors: Prof. Yang Zhen Prof. Chen Jiahua Prof. Tang Yefeng 2015-10-05 1 Contents Background
Short Literature Presentation 10/4/2010 Erika A. Crane
Copper-Catalyzed Enantioselective Synthesis of trans-1- Alkyl-2-substituted Cyclopropanes via Tandem Conjugate Additions-Intramolecular Enolate Trapping artog, T. D.; Rudolph, A.; Macia B.; Minnaard, A.
PhD research with Prof. Lutz H. Gade at the Univ. of Strasbourg. Postdoc in 2003 with Andreas Pfaltz (Basel Switzerland)
idium-catalyzed Asymmetric Isomerization of rimary Allylic Alcohols Mantilli, L., Gerard, D., Torche, S., Besnard, C., Mazet * C. Angew. Chem. Int. Ed., 2009, 48, 1-6 1,n-Glycols as Dialdehyde Equivalents
Problem Set 2: Reactions of Carbocations - KEY
Problem Set 2: eactions of Carbocations - KEY Due Tuesday, 10/11/16 1. a. Formation of 1 and 2 silyl ethers is always high-yielding, but selective silylation of a single hydroxyl group can be challenging.
Electrophilic Carbenes
Electrophilic Carbenes The reaction of so-called stabilized diazo compounds with late transition metals produces a metal carbene intermediate that is electrophilic. The most common catalysts are Cu(I)
Mild Cobalt-Catalyzed Hydrocyanation of Olefins with Tosyl Cyanide
Mild Cobalt-Catalyzed ydrocyanation of lefins with Tosyl Cyanide 1 3 2 + Ts Co cat., Si 3 Et, 1-3 h, T 1 2 3 Gaspar, B.; Carreira, E. M. Angew. Chem. Int. Ed. ASAP Current Literature Kalyani Patil 12 May
Suggested solutions for Chapter 41
s for Chapter 41 41 PBLEM 1 Explain how this synthesis of amino acids, starting with natural proline, works. Explain the stereoselectivity of each step after the first. C 2 C 2 3 CF 3 C 2 2 Pd 2 C 2 +
Total Synthesis of (+)-Gelsemine. Xuan Dong group seminar 12/19/2012
Total Synthesis of (+)-Gelsemine Xuan Dong group seminar 12/19/2012 Historical Background of Gelsemine First detected the presence of alk aloids in extracts of G. sempervir ens in 1870 by Wormley. 1876,
Homogeneous Catalysis - B. List
omogeneous Catalysis - B. List 2.2.2 Research Area "rganocatalytic Asymmetric α-alkylation of Aldehydes" (B. List) Involved:. Vignola, A. Majeed Seayad bjective: α-alkylations of carbonyl compounds are
CHEM 251 (4 credits): Description
CHEM 251 (4 credits): Intermediate Reactions of Nucleophiles and Electrophiles (Reactivity 2) Description: An understanding of chemical reactivity, initiated in Reactivity 1, is further developed based
David W.C. MacMillan: Career-in-Review. Yan Xu Dong Group Meeting Jan. 2, 2014
David W.C. MacMillan: Career-in-Review Yan Xu Dong Group Meeting Jan. 2, 2014 David W.C. MacMillan: A Brief Introduction Career 1968 Born in Bellshill, Scotland. 1987-1991 Undergraduate degree in chemistry
molecules ISSN by MDPI
, 993-997 molecules ISS 1420-3049 2000 by MDPI http://www.mdpi.org Lewis Acid Catalysis of the Diels Alder Reaction Using iobium and Tantalum Chlorides in the Presence of Coordinating Ligands Joshua owarth*
A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones and Aldehydes
A ighly Efficient rganocatalyst for Direct Aldol Reactions of Ketones and Aldehydes Zhuo Tang, Zhi-ua Yang, Xiao-ua Chen, Lin-Feng Cun, Ai-Qiao Mi, Yao-Zhong Jiang, and Liu-Zhu Gong Contribution from the
ChiralIonic Liquids. An Adolescent Technology. Jeremy Henle 1/24/12
ChiralIonic Liquids An Adolescent Technology Jeremy Henle 1/24/12 Strategies in Asymmetric Synthesis Chiral Induction Starting Materials Chiral Catalysts Chiral Solvents Enantioenriched Chiral Auxillaries
A Simple Introduction of the Mizoroki-Heck Reaction
A Simple Introduction of the Mizoroki-Heck Reaction Reporter: Supervisor: Zhe Niu Prof. Yang Prof. Chen Prof. Tang 2016/2/3 Content Introduction Intermolecular Mizoroki-Heck Reaction Intramolecular Mizoroki-Heck
Tips for taking exams in 852
Comprehensive Tactical Methods in rganic Synthesis W. D. Wulff 1) Know the relative reactivity of carbonyl compounds Tips for taking exams in 852 Cl > > ' > > ' N2 eg: 'Mg Et ' 1equiv. 1equiv. ' ' Et 50%
A. Loupy, B.Tchoubar. Salt Effects in Organic and Organometallic Chemistry
A. Loupy, B.Tchoubar Salt Effects in Organic and Organometallic Chemistry 1 Introduction - Classification of Specific Salt Effects 1 1.1 Specific Salt Effects Involving the Salt's Lewis Acid or Base Character
Rising Novel Organic Synthesis
Literature report Rising Novel Organic Synthesis Methods Based on the Cleavage of N-N and N-O Bonds Reporter: Zhang-Pei Chen Checker : Mu-Wang Chen Date: 04/03/2014 Kürti, L. et al. Kürti, L. et al. Science
Iridium-Catalyzed Hydrogenation with Chiral P,N Ligands
Iridium-Catalyzed Hydrogenation with Chiral P, Ligands 贾佳 utline Brief Introduction Hydrogenation of C=C Bonds Hydrogenation of C= Bonds Hydrogenation of C= Bonds Conclusion Brief Introduction First example
Lewis Base Catalysis in Organic Synthesis
Hu Group Lewis Base Catalysis in Organic Synthesis Group Meeting Yuwen Zeng Sep. 28 th, 2014 Introduction Definitions Basic concepts Presentation Outline Lewis base catalysis: n- * Interactions Electrophilic
Development of Chiral Phosphine Olefin Ligands and Their Use in Asymmetric Catalysis
Development of Chiral osphine lefin Ligands and Their Use in Asymmetric Catalysis 2 Wei-Liang Duan July 31, 2007 Research Works in Hayashi Group, Kyoto University (ct, 2003 Mar, 2007) Conventional Chiral
Initials: 1. Chem 633: Advanced Organic Chemistry 2011 Final Exam
Initials: 1 ame: Chem 633: Advanced rganic Chemistry 2011 Final Exam Please answer the following questions clearly and concisely. In general, use pictures and less than 10 words in your answers. Write
Total Synthesis of the Protected Aglycon of Fidaxomicin (Tiacumicin B, Lipiarmycin A3)
Total Synthesis of the Protected Aglycon of Fidaxomicin (Tiacumicin B, Lipiarmycin A3) H. Miyatake-Ondozabal, E. Kaufmann, K.Gademann* Angew. Chem. Int. Ed. 2015, 54, 1933 1936 06.08.2015 Literature Presentation
Total synthesis of Spongistatin
Literature Semminar 1. Introduction: Total synthesis of Spongistatin Chen Zhihua (M2) Isolation: Pettit et al. J. rg. Chem. 1993, 58, 1302. Kitagawa et al. Tetrahedron Lett. 1993, 34, 1993. Fusetani et
Corey-Bakshi. Bakshi-Shibata Reduction. Name Reaction Nilanjana Majumdar
Corey-Bakshi Bakshi-Shibata Reduction Name Reaction Nilanjana Majumdar 02.27.09 utline Introduction Background CBS Reaction Application to Synthesis Introduction Born: 12 th July, 1928 in Methuen, Massachusetts,
The aza-baylis-hillman Reaction: Mechanism, Asymmetric Catalysis, & Abnormal Adducts. Larry Wolf SED Group Meeting
The aza-baylis-hillman Reaction: Mechanism, Asymmetric Catalysis, & Abnormal Adducts Larry Wolf SED Group Meeting 04-10-07 Outline Brief historical account and Utility Mechanism Different methods for asymmetric
Rhodium-Catalyzed Enantioselective
Rhodium-Catalyzed Enantioselective Isomerization of Oxabicycles Reporter: Jie Wang Checker: Shubo Hu Date: 2017-07-03 Yen, A.; Choo, K.-L.; Yazdi, S. K.; Franke, P. T.; Webster, R.; Franzoni, I.; Loh,
Literature Report 3. Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A. Date :
Literature Report 3 Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A Reporter : Xiao-Yong Zhai Checker : Shubo u Date : 2017-10-30 Pritchett, B. P.; Donckele, E. J.; Stoltz, B. M. Angew.
The Synthesis of Molecules Containing Quaternary Stereogenic Centers via the Intramolecular Asymmetric Heck Reaction
The Synthesis of Molecules Containing Quaternary Stereogenic Centers via the Intramolecular Asymmetric Heck Reaction Reported by Eric P. Gillis April 19, 2007 INTRODUCTION The enantioselective synthesis
Chiral Diol Promoted Boronates Addi3on Reac3ons. Lu Yan Morken Group Boston College
Chiral Diol Promoted Boronates Addi3on Reac3ons Lu Yan Morken Group Boston College Main Idea R R B or R R B Ar * exchange B * * or B Ar R 1 R 1 R 2 R 1 R 2 Products not nucleophilic enough nucleophilic
Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo
Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo 2014.1.6 1 Content Introduction Progress of Catellani Reaction o-alkylation and Applications o-arylation and Applications Conclusion and Outlook
Morita Baylis Hillman Reaction. Aaron C. Smith 11/10/04
Morita Baylis Hillman Reaction Aaron C. Smith 11/10/04 Outline 1. Background 2. Development of Asymmetric Variants 3. Aza-Baylis Hillman Reaction 4. Applications of Baylis Hillman Adducts Outline 1. Background
Organic Chemistry I (Chem340), Spring Final Exam
rganic Chemistry I (Chem340), pring 2005 Final Exam This is a closed-book exam. No aid is to be given to or received from another person. Model set and calculator may be used, but cannot be shared. Please
Lecture 6: Transition-Metal Catalysed C-C Bond Formation
Lecture 6: Transition-Metal Catalysed C-C Bond Formation (a) Asymmetric allylic substitution 1 u - d u (b) Asymmetric eck reaction 2 3 Ar- d (0) Ar 2 3 (c) Asymmetric olefin metathesis alladium π-allyl
Strained Molecules in Organic Synthesis
Strained Molecules in rganic Synthesis 0. Introduction ~ featuring on three-membered rings ~ Tatsuya itabaru (M) Lit. Seminar 08068 for cyclobutadienes : see Mr. Yamatsugu's Lit. Sem. 069 eat of Formation
Chapter 14. Principles of Catalysis
Organometallics Study Meeting 2011/08/28 Kimura Chapter 14. Principles of Catalysis 14. 1. General Principles 14.1.1. Definition of a Catalyst 14.1.2. Energetics of Catalysis 14.1.3. Reaction Coordinate
Dual enantioselective control by heterocycles of (S)-indoline derivatives*
Pure Appl. Chem., Vol. 77, No. 12, pp. 2053 2059, 2005. DOI: 10.1351/pac200577122053 2005 IUPAC Dual enantioselective control by heterocycles of (S)-indoline derivatives* Yong Hae Kim, Doo Young Jung,
Alkenes, Important Synthetic Intermediates.
UTLIE 535 SESSI 08 (2007) Page 73 Alkenes, Important Synthetic Intermediates. 1. We have discussed the synthesis of alkenes. 1.1. There are many more protocols than the ones we have discussed. 1.2. Some
Organocatalytic stereoselective [8+2] and [6+4] cycloadditions
![Organocatalytic stereoselective [8+2] and [6+4] cycloadditions](/thumbs/85/92727022.jpg "Organocatalytic stereoselective [8+2] and [6+4] cycloadditions")
rganocatalytic stereoselective [8+2] and [6+4] cycloadditions Joel Walker Current Literature March 4 th, 2017 Mose, R.; Preegel, G.; Larsen, J.; Jakobsen, S.; Iversen, E..; Jørgensen, K. A. Nature Chem.
Chiral Amplification. Literature Talk Fabian Schneider Konstanz, Universität Konstanz
Chiral Amplification Literature Talk Fabian Schneider Konstanz, 18.10.2017 Overview 1) Motivation 2) The nonlinear Effect in asymmetric catalysis - First encounters - Basic principles - Formalization and
CHEM 330. Topics Discussed on Nov. 25
CM 330 Topics Discussed on Nov. 25 A typical cycloaddition process leading to C C bond formation: the Diels-Alder reaction between an appropriately substituted 1,3-butadiene and an alkene: R 1 R 2 heat
Reactivity within Confined Nano-spaces
Reactivity within Confined Nano-spaces Larry Wolf Group Meeting 11-17-09 Encapsulating Cyclobutadiene hemicarcerand Anslyn, E. V; Dougherty, D. A. Modern Physical Organic Chemistry Cram. D. J. et. al.
Additions to Metal-Alkene and -Alkyne Complexes
Additions to tal-alkene and -Alkyne Complexes ecal that alkenes, alkynes and other π-systems can be excellent ligands for transition metals. As a consequence of this binding, the nature of the π-system
Rhodium Catalyzed Alkyl C-H Insertion Reactions
Rhodium Catalyzed Alkyl C-H Insertion Reactions Rh Rh Jeff Kallemeyn 5/17/05 1. Cyclopropanation The Versatile and Reactive Rhodium Carbene R + Et Rh 2 (Ac) 4 R C 2 Et N 2 2. [2,3] sigmatropic rearrangement
Halogen Bond Applications in Organic Synthesis. Literature Seminar 2018/7/14 M1 Katsuya Maruyama
Halogen Bond Applications in Organic Synthesis Literature Seminar 2018/7/14 M1 Katsuya Maruyama 1 Contents 1. Introduction 2. Property of Halogen Bond 3. Application to Organic Synthesis 2 1. Introduction
Nucleophilic Heterocyclic Carbene Catalysis. Nathan Werner Denmark Group Meeting September 22 th, 2009
Nucleophilic Heterocyclic Carbene Catalysis Nathan Werner Denmark Group Meeting September 22 th, 2009 Thiamine Thiamine Vitamin B 1 The first water-soluble vitamin described Is naturally synthesized by
Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of gamma-thioesters
Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of gamma-thioesters The MIT Faculty has made this article openly available. Please share how this access benefits you.
New cyclizations via catalytic ruthenium vinylidenes*
Pure Appl. Chem., Vol. 80, No. 5, pp. 1167 1177, 2008. doi:10.1351/pac200880051167 2008 IUPAC New cyclizations via catalytic ruthenium vinylidenes* Jesús A. Varela, Carlos González-Rodríguez, Silvia G.
Guideline 5: Tactical Bonds
Guideline 5: Tactical Bonds f the molecule contains more than one functional group and hence there is a choice of which bonds to disconnect, how do you decide? Practice, but here are a few rough guidelines
Back to Sugars: Enzymatic Synthesis
Back to Sugars: Enzymatic Synthesis Zhensheng Ding ov. 04 orthrup, A. B.; M acm illan, D. W. C. Science 2004, 305, 1752 orthrup, A. B. and MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799 orthrup,
CHEM 203. Final Exam December 18, This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Final Exam December 18, 2013 Your name: This a closed-notes, closed-book exam You may use your set of molecular models This test consists of 10 pages Time: 2h 30 min 1. / 20 2. / 20 3. / 30 4.
[3,3]-sigmatropic Processes. [2,3]-sigmatropic Processes. Ene Reactions. Generalized Sigmatropic Processes X,Y=C, N, O, S X,Y=C, N, O, S
![[3,3]-sigmatropic Processes. [2,3]-sigmatropic Processes. Ene Reactions. Generalized Sigmatropic Processes X,Y=C, N, O, S X,Y=C, N, O, S](/thumbs/94/119475672.jpg "[3,3]-sigmatropic Processes. [2,3]-sigmatropic Processes. Ene Reactions. Generalized Sigmatropic Processes X,Y=C, N, O, S X,Y=C, N, O, S")
Generalized igmatropic Processes [3,3]-sigmatropic Processes 1 3,=C,,, 1 3 3,=C,,, 3 [2,3]-sigmatropic Processes 1 3,=C,,, 1 3 Ene eactions 1 3 1 3 Cope earrangement [3,3]- igmatropic earrangements Transition
Contents to Volume 2. Contents to Volume 1
to Volume 2 to Volume 1 X 7 Transition Metal-Catalyzed Desulfitative Coupling of Thioorganic Compounds with Boronic Acids 363 Ethel C. Garnier-Amblard and Lanny S. Liebeskind 7.1 General Introduction 363
Catalytic Enantioselective Diels-Alder Reactions Chwee T.S 1 and Wong M.W 2
Catalytic Enantioselective Diels-Alder Reactions Chwee T.S 1 and Wong M.W 2 Department of Chemistry,Faculty of Science, National University of Singapore 10 Kent Ridge Road, Singapore 117546 Abstract Theoretical
Chemistry 335 Supplemental Slides: Interlude 1. Reduction: addition of hydrogen to the substrate. Oxidation: addition of oxygen to the substrate
Interlude 1: Oxidations, Reductions & Other Functional Group Interconversions (FGI) 1. Definition of Oxidation and Reduction For practical purposes in organic chemistry, oxidation and reduction are defined
Page 1 of 9. Sessional Examination (November 2017) Max Marks: 20 Date: Time: One Hour. Model Answers
Page 1 of 9 Sessional Examination (November 2017) Class: B. Pharm-II yr (III sem) Subject: Pharma Org. Chem-II Max Marks: 20 Date: 14.11.2017 Time: One Hour Model Answers Q. 1. Solve the following (ANY
Organic Synthesis III 8 x 1hr Lectures: Michaelmas Term Weeks 5-8 Tues; Thrs at 10am Dyson Perrins lecture theatre
Organic Synthesis III 8 x 1hr Lectures: Michaelmas Term Weeks 5-8 Tues; Thrs at 10am Dyson Perrins lecture theatre Copies of this handout will be available at http://donohoe.chem.ox.ac.uk/page16/index.html
Carbonyl Ylide Cycloadditions
Carbonyl Ylide Cycloadditions cond. icholas Anderson Denmark Group eting 07/13/10 Carbonyl Ylides Uncharged 1,3-Dipole Conjugated π-system ighly reactive on-isolable Generate in-situ Carbonyl Ylide Stability
Heterogeneous chiral catalysis on surfaces, in nanopores and with emulsions
Prof. Can Li's Laboratory Heterogeneous chiral catalysis on surfaces, in nanopores and with emulsions Chiral catalysis is of great industrial interest for the production of enantiomerically pure compounds.