Selectivity and Natural Product Synthesis. Reporter: Liang Xin-ting Supervisors: Prof. Yang Prof. Chen Prof. Tang
|
|
|
- Constance Haynes
- 5 years ago
- Views:
Transcription
1 Selectivity and Natural Product Synthesis Reporter: Liang Xin-ting Supervisors: Prof. Yang Prof. Chen Prof. Tang
2 Content Introduction Selectivity of oxidative coupling Chemoselectivity Regioselectivity Diastereoselectivity Enantioselectivity Natural Product Synthesis Summary & Outlook Acknowledgement 2
3 Content Introduction Selectivity of oxidative coupling Chemoselectivity Regioselectivity Diastereoselectivity Enantioselectivity Natural Product Synthesis Summary & Outlook Acknowledgement 3
4 Introduction Cross coupling reaction Oxidative coupling Nucleophiles are likely the most abundant chemicals applied in synthesis and widely exist in nature, such as hydrocarbons. Side reaction: homo-coupling & direct reaction of nucleophiles and oxidant. Shi, W.; Liu, C.; Lei, A. Chemical Society Reviews 2011, 40,
5 Introduction Oxidative coupling reaction Shi, W.; Liu, C.; Lei, A. Chemical Society Reviews 2011, 40,
6 Introduction Molecules containing 1,4-dicarbonyl moieties Abundant Accessible DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130,
7 Introduction Molecules containing indole moieties Richter, J. M.; Whitefield, B. W.; Maimone, T. J.; Lin, D. W.; Castroviejo, M. P.; Baran, P. S. J. Am. Chem. Soc. 2007, 129,
8 Introduction Synthesis of 1,4-dicarbonyl compounds DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130,
9 Introduction Synthesis of indole containing compounds Richter, J. M.; Whitefield, B. W.; Maimone, T. J.; Lin, D. W.; Castroviejo, M. P.; Baran, P. S. J. Am. Chem. Soc. 2007, 129,
10 Introduction History of oxidative coupling of enolates DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130,
11 Introduction Mechanism of oxidative coupling of enolates DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130,
12 Introduction History of oxidative coupling of enolates I2 as oxidant Langer, T.; Illich, M.; Helmchen, G. Synlett 1996, 1996,
13 Introduction Possible reactions to compete with hetero-coupling DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130,
14 Content Introduction Selectivity of oxidative coupling Chemoselectivity Regioselectivity Diastereoselectivity Enantioselectivity Natural Product Synthesis Summary & Outlook Acknowledgement 14
15 Chemoselectivity Condensation reactions DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, Homo-/Hetero-coupling (oxidation potentials) Baciocchi, E.; Casu, A.; Ruzziconi, R. Tetrahedron Lett. 1989, 30, Paolobelli, A. B.; Latini, D.; Ruzziconi, R. Tetrahedron Lett. 1989,
16 Chemoselectivity Homo-/Hetero- coupling 1.0 eq. each coupling partner DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, Richter, J. M.; Whitefield, B. W.; Maimone, T. J.; Lin, D. W.; Castroviejo, M. P.; Baran, P. S. J. Am. Chem. Soc. 2007, 129,
17 Chemoselectivity Homo-/Hetero- coupling LDA, LHMDS, THF for most case. Diisopropylamine and I2 may form charge-transfer complex. Changing the cation (i.e., Na, K) only proved detrinental to the yield. Phil S. Baran Fan, F.; Xie, W.; Ma, D. Org. Lett. 2012, 14, Richter, J. M.; Whitefield, B. W.; Maimone, T. J.; Lin, D. W.; Castroviejo, M. P.; Baran, P. S. J. Am. Chem. Soc. 2007, 129,
18 Chemoselectivity Homo-/Hetero- coupling Aggregation of metal (Li +) enolate Similar pka, Similar relative rates of oxidation. When one enolate is sterically encumbered, A2B2 is major. Casey, B. M.; Flowers, R. A. J. Am. Chem. Soc. 2011, 133,
19 Chemoselectivity Homo-/Hetero- coupling Aggregation of metal (Li +) enolate Casey, B. M.; Flowers, R. A. J. Am. Chem. Soc. 2011, 133,
20 Chemoselectivity Homo-/Hetero- coupling oxidation potentials Aggregation of metal enolate Intramolecular for hetero-coupling Avetta Jr, C. T.; Konkol, L. C.; Taylor, C. N.; Dugan, K. C.; Stern, C. L.; Thomson, R. J. Org. Lett. 2008, 10,
21 Regioselectivity Steric factor:coupling side Ito, Y.; Konoike, T.; Harada, T.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, Frazier Jr, R. H.; Harlow, R. L. The Journal of Organic Chemistry 1980, 45,
22 Diastereoselectivity Syn(dl) & anti (meso) Flaver to some extent Csákÿ, A. G.; Plumet, J. Chemical Society Reviews 2001, 30, 313. Avetta Jr, C. T.; Konkol, L. C.; Taylor, C. N.; Dugan, K. C.; Stern, C. L.; Thomson, R. J. Org. Lett. 2008, 10,
23 Diastereoselectivity Syn(dl) & anti (meso) Avetta Jr, C. T.; Konkol, L. C.; Taylor, C. N.; Dugan, K. C.; Stern, C. L.; Thomson, R. J. Org. Lett. 2008, 10,
24 Diastereoselectivity Syn(dl) & anti (meso) Syn Anti Avetta Jr, C. T.; Konkol, L. C.; Taylor, C. N.; Dugan, K. C.; Stern, C. L.; Thomson, R. J. Org. Lett. 2008, 10,
25 Enantioselectivity N-Acyloxazolidinones DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130,
26 Enantioselectivity N-Acyloxazolidinones DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130,
27 Ichikawa, M.; Takahashi, M.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2004, 126,
28 Enantioselectivity Imidazolidinone Jang, H.-Y.; Hong, J.-B.; MacMillan, D. W. J. Am. Chem. Soc. 2007, 129,
29 Enantioselectivity Imidazolidinone Jang, H.-Y.; Hong, J.-B.; MacMillan, D. W. J. Am. Chem. Soc. 2007, 129,
30 Catalytic Version Zn ll, Cu ll, O2 system Do, H.-Q.; Tran-Vu, H.; Daugulis, O. Organometallics 2012, 31,
31 Content Introduction Selectivity of oxidative coupling Chemoselectivity Regioselectivity Diastereoselectivity Enantioselectivity Natural Product Synthesis Summary & Outlook Acknowledgement 31
32 Natural Product Synthesis Inter-molecular oxidative coupling Krawczuk, P. J.; Scho ne, N.; Baran, P. S. Org. Lett. 2009, 11, Konkol, L. C.; Guo, F.; Sarjeant, A. A.; Thomson, R. J. Angew. Chem. Int. Ed. 2011, 50,
33 Natural Product Synthesis Inter-molecular oxidative coupling Richter, J. M.; Ishihara, Y.; Masuda, T.; Whitefield, B. W.; Llamas, T.; Pohjakallio, A.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 33
34 Natural Product Synthesis Intra-molecular oxidative coupling Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128,
35 Natural Product Synthesis Intra-molecular oxidative coupling Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128,
36 Natural Product Synthesis Intra-molecular oxidative coupling Zi, W.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2012, 134,
37 Natural Product Synthesis Intra-molecular oxidative coupling Zuo, Z.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2010, 132,
38 Content Introduction Selectivity of oxidative coupling Chemoselectivity Regioselectivity Diastereoselectivity Enantioselectivity Natural Product Synthesis Summary & Outlook Acknowledgement 38
39 Summary & Outlook Mechanism research and substrate extension; Natural products synthesis 39
40 Acknowledgement Prof. Yang, Prof. Chen, Prof. Tang Mr. You Lin, Mr. Li Yuan-he, Mr. Zhu Zhi-yang Members of B628 All the lab mates here 40
41 Thanks for your attention! 41
Total Synthesis and Absolute Stereochemical Assignment of ( )-Communesin F
Total Synthesis and Absolute Stereochemical Assignment of ( )-Communesin F Zhiwei Zuo, Weiqing Xie, Dawei Ma* Shanghai Institute of rganic Chemistry, Shanghai, China J. Am. Chem. Soc. 2010, 132, 13226-13228.
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
Copper-Catalyzed Aerobic Oxidative C-H Functionalizations. Supervisor: Prof. Yong Huang Reporter: Weiyu Yin ( 殷韦玉 ) Date:
Copper-Catalyzed Aerobic Oxidative C-H Functionalizations Supervisor: Prof. Yong Huang Reporter: Weiyu Yin ( 殷韦玉 ) Date: 2013-04-08 0 Content Introduction C-H Oxidation Initiated by Single-Electron Transfer(SET)
C H activation of aliphatic amines without unnecessary mask M2 Takaya Togo
C H activation of aliphatic amines without unnecessary mask 2017.11.25 M2 Takaya Togo 1 Outline 1.Introduction 2.Free amines as DG Discovery of new activation mode Mechanistic studies Application of the
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.
Recent Developments in Alkynylation
--New approaches to introduce an alkynyl group Reporter: Zhao-feng Wang Supervisor: Yong Huang 2013-03-27 Contents 1. Introduction of Acetylene Chemistry 2. Nucleophilic alkynylation : Classic text book
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
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
Protecing-Group-Free Synthesis. Reporter: Zhu Zhiyang Advisor: Prof Yang Prof Chen Prof Tang Date:
Protecing-Group-Free Synthesis Reporter: Zhu Zhiyang Advisor: Prof Yang Prof Chen Prof Tang Date: 2015.05.19 1 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples
Oxidative Enolate Coupling in Total Synthesis
Literature Seminar 2010.6.2 Oxidative Enolate Coupling in Total Synthesis Shi-Liang, Shi Appointment April, 2009 Member, Skaggs Institute for Chemical Biology June, 2008 Professor of Chemistry July, 2006
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
Tautomerism and Keto Enol Equilibrium
Tautomerism and Keto Enol Equilibrium Enols & enolates are important nucleophiles in organic & biochemistry. Keto-Enol Equilibrium: Tautomerisation can be catalyzed by either acids or bases. Relative stability
Palladium-catalyzed sp 3 C H activation. Yan Xu Dong Group Meeting Apr. 2, 2014
Palladium-catalyzed sp 3 C H activation, Yan Xu Dong Group Meeting Apr. 2, 2014 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation:
Review Revisiting the Baldwin s Rules Guidelines for Ring Closure Li Yuanhe Anion- 3/4 4/5 5/6 6/7 endo- -dig exo- endo- -trig exo- endo- -tet exo-
Review Revisiting the Baldwin s Rules Guidelines for Ring Closure Li Yuanhe Anion - 3/4 4/5 5/6 6/7 -trig Supervisors: Prof. Yang Prof. Chen -tet Prof. Tang Introduction (Sir) Jack Baldwin 1938, Born,
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.
Review. Recent Developments in Pd-catalyzed Carbonylation Reaction. Li Yuanhe. Supervisors: Prof. Yang Prof. Chen Prof. Tang
Review Recent Developments in Pd-catalyzed Carbonylation Reaction Li Yuanhe Supervisors: Prof. Yang Prof. Chen Prof. Tang History 1962, E. Fischer Z. Nafurforsch. 1962, 17b, 484. 1963, R. Heck J. Org.
Highlights from the MacMillan Lab. Kelly Craft Group Meeting Presentation 7/8/15
Highlights from the MacMillan Lab Kelly Craft Group Meeting Presentation 7/8/15 David MacMillan! Born in Bellshill, Scotland (1968)! Undergraduate degree: University of Gaslow (Ernie Colvin)! PhD: University
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
The Chemistry of Organozinc Reagent a long story. Reporter: Han Yixin Adivisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo Date: Nov. 22 nd.
The Chemistry of Organozinc Reagent a long story Reporter: Han Yixin Adivisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo Date: Nov. 22 nd. 2013 2 Content Introduction Reactions of Organozinc reagent
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
First Row TM Catalyzed C-H Activation. Zhi Ren 2014/9/10
First Row TM Catalyzed C-H Activation Zhi Ren 2014/9/10 Outline 1. Introduction 2. Sc catalyzed C-H activation 3. Ti catalyzed C-H activation 4. V catalyzed C-H oxidation/fluorination 5. Mn catalyzed C-H
Chapter 4 Functional Group Transformations: Oxidation and Reduction. 4.8 Terminology for Reduction of Carbonyl Compounds
Chapter 4 Functional Group Transformations: Oxidation and Reduction Oxidation states (numbers) Less E.N. than C = -1 More E.N. than C = +1 C = 0 H H H C C OH H H 4.8 Terminology for Reduction of Carbonyl
Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group. Lei Zhang 03/23/2016 Dong Group
Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group Lei Zhang 03/23/2016 Dong Group Content 1 Alkyne involved Annulation in Hua group 2 3 4 Brief Introduction of Internal Oxidants
Chiral Supramolecular Catalyst for Asymmetric Reaction
Chiral Supramolecular Catalyst for Asymmetric Reaction 2017/1/21 (Sat.) Literature Seminar Taiki Fujita (B4) 1 Introduction Rational design of chiral ligands remains very difficult. Conventional chiral
Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C H Borylation
Enabled by Ligand-Controlled C H Borylation Yu Feng, Dane Holte, Jochen Zoller, Shigenobu Umemiya, Leah R. Simke, and Phil S. Baran J. Am. Chem. Soc. 2015, 137, 10160 10163. I. Introduction II. Retrosynthetic
Review. Frank Glorius & His Rh(III) C-H Activation. Li Yuanhe. Supervisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo 1 /21
Review Frank Glorius & His Rh(III) C-H Activation Li Yuanhe Supervisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo 1 /21 Author Introduction Prof. Dr. Frank Glorius 1972 Born 1991-1992 Military service
Oxidative couplings of two nucleophiles
Oxidative Couplings of Hydrocarbons Oxidative couplings of two nucleophiles Oxidants involved: O 2 H 2 O 2 high h valent metals(copper salts) halides(iodine(Ⅲ) oxidants) Lei, A. W. Chem. Rev., 2011, 111,
Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang!
1! Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang! 2! utline! 1. Brief Introduction! 2. ucleophilic Dominoes! 3. Electrophilc Dominoes! 4. Radical
The Vinylogous Aldol Reaction
The Vinylogous Aldol Reaction Reporter: Sixuan Meng Supervisor: Prof. Huang 2013-09-09 Zanardi, F. et al. Chem. Rev. 2000, 100, 1929 Zanardi, F. et al.. Chem. Rev. 2011, 111, 3076 Introduction 2 3 Regiochemical
Cambrian Explosion, Complex Eukaryotic Organism, Ozonosphere 3
Reporter: Wang Yuefan Reporter: Wang Yuefan Supervisor: Prof. Yang Zhen Supervisor: Prof. Yang Zhen Prof. Chen Jiahua Prof. Chen Jiahua 1 2011-12-2727 2011-02 2012-03 02-25 03-23 25 Content Preface Nature
Advanced Organic Chemistry
D. A. Evans, G. Lalic Chem 530A Chemistry 530A Advanced Organic Chemistry Lecture notes part 8 Carbanions Organolithium and Grignard reagents Organocopper reagents 1. Direct metalation 2. From radical
I. Introduction. Peng Zhao. Liu lab
Asymmetric Total Synthesis of Mycoleptodiscin A Shupeng Zhou, Hao Chen, Yijie Luo, Wenhao Zhang and Ang Li Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai
Highlights of Schmidt Reaction in the Last Ten Years
ighlights of Schmidt eaction in the Last Ten Years Dendrobates histrionicus Jack Liu ov. 18, 2003 Introduction Classical Schmidt reaction of aldehydes and carboxylic acids Classical Schmidt reaction of
I. Introduction. II. Retrosynthetic Analysis. Andrew Baggett. Liu lab
Total Synthesis of Limonin Shuji Yamashita,* Akito Naruko, Yuki Nakazawa, Le Zhao, Yujiro Hayashi, Masahiro Hirama Tohoku University, Department of Chemistry, Aramaki-aza aoba, Aoba-ku, Sendai 980-8578
Asymmetric Alklylation of Enolates
Asymmetric Alklylation of Enolates M with material from A G Meyers http://faculty.chemistry.harvard.edu/myers/pages/chem-215-handouts 745 rganic Synthesis Spring 2015 Asymmetric Alkylation - eed to control
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
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
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
Stereoselective reactions of enolates
1 Stereoselective reactions of enolates Chiral auxiliaries are frequently used to allow diastereoselective enolate reactions Possibly the most extensively studied are the Evan s oxazolidinones These are
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
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.
Functionalization of arene and heteroarene via organic photoredox catalysis. Reporter: Fengjin Wu Supervisor: Prof. Huang Date:
Functionalization of arene and heteroarene via organic photoredox catalysis Reporter: Fengjin Wu Supervisor: Prof. Huang Date: 10. 23. 2017 Outline: 1. Background 2. Direct C-H bond functionalization of
Iron Catalysed Coupling Reactions
LONG LITERATURE REPORT Iron Catalysed Coupling Reactions Mingyu Liu 2017. 8. 31 1 Fe [Ar]3d 6 4s 2 The fourth most common element in the Earth s crust Relatively less understanding and manipulation of
The Story of Azadirachtin. Weiwu Ren
The Story of Azadirachtin Weiwu Ren 2015-12-17 Content 1 Introduction 2 Isolation and Structure Determination 3 Synthetic Study towards Azadirachtin 4 Total Synthesis of Azadirachtin Ley s Work Watanabe
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
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
Self-stable Electrophilic Reagents for Trifluoromethylthiolation. Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date:
Self-stable Electrophilic Reagents for Trifluoromethylthiolation Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date: 2017-12-25 Content Introduction Trifluoromethanesulfenates: Preparation and reactivity
Chromium Arene Complexes
Go through Reviews Chem. Reviews Chem. Soc. Reviews Book by Prof. A. J. Elias Chromium Arene Complexes Complexation of Cr(CO) 3 with ARENES Chromium arene complexes Metal complexation is appealing in organic
Few Selected Total Synthesis in Group Meeting June 1, Anil Kumar Gupta
Few Selected Total Synthesis in 2007 Group Meeting June 1, 2007 Anil Kumar Gupta Total Synthesis without Protecting Groups Chemoselectivity!! Solution: Protecting group BUT..It adds. Cost Complexity of
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
Cornforth: Nature is an organic chemist with a preference for the aldol reaction.
I. Basic Principles IC. The Aldol Reaction Cornforth: Nature is an organic chemist with a preference for the aldol reaction. Many natural products contain polyhydroxylated carbon arrays, usually a mix
Aldehydes and Ketones : Aldol Reactions
Aldehydes and Ketones : Aldol Reactions The Acidity of the a Hydrogens of Carbonyl Compounds: Enolate Anions Hydrogens on carbons a to carbonyls are unusually acidic The resulting anion is stabilized by
Iron Catalysis in Organic Synthesis Multitasking Champion. Current literature Andrey Kuzovlev
Iron Catalysis in Organic Synthesis Multitasking Champion Current literature Andrey Kuzovlev 02.03.2017 Introduction Readily available, cheap, relatively nontoxic, 1.300 ppm residual iron is acceptable
Palladium-catalyzed alkylation of unactivated olefins*
Pure Appl. Chem., Vol. 76, No. 3, pp. 671 678, 2004. 2004 IUPAC Palladium-catalyzed alkylation of unactivated olefins* Ross A. Widenhoefer P. M. Gross Chemical Laboratory, Duke University, Durham, NC 27708-0346,
Chiral Catalyst II. Palladium Catalysed Allylic Displacement ( -allyl complexes) 1. L n Pd(0) 2. Nuc
Chiral Catalyst II ast lecture we looked at asymmetric catalysis for oxidation and reduction Many other organic transformations, this has led to much investigation Today we will look at some others...
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
Organic Reactions catalyzed by rhenium carbonyl complexes
Organic Reactions catalyzed by rhenium carbonyl complexes Fanyang Mo Dong group seminar Feb. 26, 2014 Ref: Kuninobu, Y.; Takai, K. Chem Rev. 2011, 111, 1938. 1 Accidentally found by Ogawa in 1908, and
Boron containing 1,1-Dimetallicalkane Reagents
Boron containing 1,1-Dimetallicalkane Reagents Topic Talk Xun Liu July 25, 2013 Outline 1. 1,1-Borio-lithioalkane reagents 2. 1,1-Boronalkane reagents 3. 1,1-Borio-zincioalkane Reagents and 1,1-Borio-cuprioalkane
Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-
Literature Report Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)- aseseazines A and B Reporter: Mu-Wang Chen Checker: Zhang-Pei Chen Date: 2013-05-28 Reisman,
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
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
Department of Chemistry, University of Saskatchewan Saskatoon SK S7N 4C9, Canada. Wipf Group. Tyler E. Benedum Current Literature February 26, 2005
Ward, D.E; Jheengut, V.; Akinnusi, O.T. Enantioselective Direct Intermolecular Aldol Reactions with Enantiotopic Group Selectivity and Dynamic Kinetic Resolution, Organic Letters 2005, ASAP. Department
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
Stereoselective reactions of enolates: auxiliaries
1 Stereoselective reactions of enolates: auxiliaries Chiral auxiliaries are frequently used to allow diastereoselective enolate reactions Possibly the most extensively studied are the Evan s oxazolidinones
Grob Fr agmentations. Dan Tao Overman Group Meeting 9/24/12
: Grob Fr agmentations Dan Tao Overman Group Meeting 9/24/12 What is a Grob Fragmentation? Heterolytic fragmentation is certain combinations of carbon and hetero atoms which undergo a regulated cleavage
The aldol reaction with metal enolates proceeds by a chair-like, pericyclic process: favored. disfavored. favored. disfavored
The aldol reaction with metal enolates proceeds by a chair-like, pericyclic process: Z-enolates: M 2 M 2 syn 2 C 2 favored 2 M 2 anti disfavored E-enolates: M 2 2 C 3 C 3 C 2 favored 2 M M disfavored In
Coordination-enabled one-step assembly of. ultrathin, hybrid microcapsules with. weak ph-response
Supporting Information Coordination-enabled one-step assembly of ultrathin, hybrid microcapsules with weak ph-response Chen Yang,, Hong Wu,, Xiao Yang,, Jiafu Shi*,,, Xiaoli Wang,, Shaohua Zhang, and Zhongyi
JACS ASAP Article: Published 3/12/08. Lei Jiao, Changxia Yuan and Zhi-Xiang Yu. Current Literature: 3/29/08. David Arnold
Tandem h(i)-catalyzed [(5+2)+1] Cycloaddition/Aldol eaction for the Construction of Linear Triquinane Skeleton: Total Syntheses of (+)-irsutene and (+)-1- Desoxyhypnophilin JACS ASAP Article: Published
sp 3 C-H insertion by α-oxo Gold Carbene B4 Kei Ito
1 sp 3 C-H insertion by α-oxo Gold Carbene B4 Kei Ito 2016. 1. 30 1. Introduction 2 About Carbene 3 Brief history of carbene (~2000) Carbene Neutral compounds featuring a divalent carbon atom with only
Asymmetric Palladium Catalyzed Cross-Coupling Reactions. Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1
Asymmetric Palladium Catalyzed Cross-Coupling Reactions Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1 Palladium Catalyzed Cross-Coupling Reactions 2 Kumada/Negishi Cross-Coupling Kumada:
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.
Stereoselective Organic Synthesis
Stereoselective rganic Synthesis Prabhat Arya Professor and Leader, Chemical Biology Program Dean, Academic Affairs, Institute of Life Sciences (An Associate Institute of University of yderabad Supported
Literature Report 5. Total Synthesis of Ileabethoxazole, Pseudopteroxazole, and seco-pseudopteroxazole
Literature Report 5 Total Synthesis of Ileabethoxazole, Pseudopteroxazole, and seco-pseudopteroxazole Reporter: Guang-Shou Feng Checker: Lei Shi Date: 2016-04-12 Li, A. et al. Angew. Chem. Int. Ed. 2016,
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols B() 2 H H B() 2 H H Hu, X.-D.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.
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
Radical cascade reactions triggered by single electron transfer
Radical cascade reactions triggered by single electron transfer Reporter: Leming Wang Supervisor: Prof. Yong Huang 2017.11.13 Mateusz P. Plesniak, Huan-Ming Huang and David J. Procter; Nature Reviews Chemistry
Copper-catalyzed cleavage of benzyl ethers with diacetoxyiodobenzene and p-toluenesulfonamide
General Papers ARKIVC 2008 (xii) 103-108 Copper-catalyzed cleavage of benzyl ethers with diacetoxyiodobenzene and p-toluenesulfonamide Ling He a,b, Qin Wang a, Guo-Chuan Zhou b, Lei Guo b, and Xiao-Qi
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.
Synthetically useful extrusion reactions in organic chemistry
Synthetically useful extrusion reactions in organic chemistry Reporter: Sun Baochuan Supervisors: Prof. Yang Zhen Prof. Chen Jiahua Extrusion Reactions Extrusion Reaction: An atom or group Y connected
Copper-mediated asymmetric transformations*
Pure Appl. Chem., Vol. 74, No. 1, pp. 37 42, 2002. 2002 IUPAC Copper-mediated asymmetric transformations* Alexandre Alexakis Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet,
Complex Interactions of Pillar[5]arene with Paraquats and. Bis(pyridinium) Derivatives
![Complex Interactions of Pillar[5]arene with Paraquats and. Bis(pyridinium) Derivatives](/thumbs/94/119880372.jpg "Complex Interactions of Pillar[5]arene with Paraquats and. Bis(pyridinium) Derivatives")
Electronic supplementary information Complex Interactions of Pillar[5]arene with Paraquats and Bis(pyridinium) Derivatives Chunju Li,* Qianqian Xu, Jian Li, Feina Yao and Xueshun Jia* Department of Chemistry,
1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions
1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions 2. Copper Catalyzed One-Pot Synthesis of Multisubstituted Quinolinones Hao Wang Denmark Group Presentation
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
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,
Xuefeng Jiang Professor Education Academic Career Awards International Invited Lecture USA Germany Shanghai Taiwan Singapore)
Xuefeng Jiang( 姜雪峰 ) Professor East China Normal University, 200062, Shanghai, China Tel: +86-21-52133654 E-mail: xfjiang@chem.ecnu.edu.cn Web: http://faculty.ecnu.edu.cn/s/641/main.jspy Education 1999-2003
Enantioselective photochemistry. Zhe Dong
Enantioselective photochemistry Zhe Dong 2014-01-15 Introduction of Circular Polarization Light Left-CPL- S light Chiral light -> Chiral Product? Right-CPL- R light Introduction of Non-Linear Effects 20%ee
Macrocycles: From Molecules to Materials. Outline
PKU CCME OPSS Shape-Persistent Macrocycles: From Molecules to Materials Jin-Liang Wang Supervisor: Jian Pei 2005. 12. 9 Outline Introduction Properties of the Shape-Persistent Macrocycles Synthetic Strategies
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
Aldol Reactions pka of a-h ~ 20
Enolate Anions Chapter 17 Hydrogen on a carbons a to a carbonyl is unusually acidic The resulting anion is stabilized by resonance to the carbonyl Aldehydes and Ketones II Aldol Reactions pka of a-h ~
"-Amino Acids: Function and Synthesis
"-Amino Acids: Function and Synthesis # Conformations of "-Peptides # Biological Significance # Asymmetric Synthesis Sean Brown MacMillan Group eting ovember 14, 2001 Lead eferences: Cheng,. P.; Gellman,
Metal Catalyzed Outer Sphere Alkylations of Unactivated Olefins and Alkynes
Metal Catalyzed uter Sphere Alkylations of Unactivated lefins and Alkynes Stephen Goble rganic Super-Group Meeting Literature Presentation ctober 6, 2004 1 utline I. Background Introduction to Carbometallation
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
Use of Cp 2 TiCl in Synthesis
Use of 2 TiCl in Synthesis eagent Control of adical eactions Jeff Kallemeyn May 21, 2002 eactions of 2 TiCl 1. Pinacol Coupling H H H 2. Epoxide pening H H E H Chemoselectivity Activated aldehydes (aromatic,
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
Metal-catalyzed asymmetric hetero-diels-alder reactions of unactivated dienes with glyoxylates
Pure & Appl. Chern., Vol. 70, No. 5, pp. 11 17-1 122, 1998. Printed in Great Britain. (0 1998 IUPAC Metal-catalyzed asymmetric hetero-diels-alder reactions of unactivated dienes with glyoxylates Mogens
Strategies for Catalytic Asymmetric Electrophilic a Halogenation of Carbonyl Compounds
Strategies for Catalytic Asymmetric Electrophilic a alogenation of Carbonyl Compounds 1 2 Y Catalyst [X + ] 1 X! 2 Y intermann, L. ; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359 4362 amashima, Y.; Sodeoka,
Zr-Catalyzed Carbometallation
-Catalyzed Carbometallation C C C C ML n C C ML n ML n C C C C ML n ML n C C ML n Wipf Group esearch Topic Seminar Juan Arredondo November 13, 2004 Juan Arredondo @ Wipf Group 1 11/14/2004 Carbometallation
Recent Advances in C-B Bond Formation through a Free Radical Pathway
Recent Advances in C-B Bond Formation through a Free Radical Pathway G. Yan. D. Huang, X. Wu, Adv. Synth. Catal. 2017, 359, 188. Daniel Meyer University of Bern 18.01.2018, Topic Review Classical Methodes
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,
Topic Review Group meeting
Topic Review Group meeting Memory of chirality Christian Gloor Based on: Zhao, H.; Hsu, D. C.; Carlier, P.R. Synthesis 2005,1, 1. Table of content > Definitions of memory of chirality > Types of chirality