Grob Fr agmentations. Dan Tao Overman Group Meeting 9/24/12
|
|
|
- Kelly Adams
- 5 years ago
- Views:
Transcription
1 : Grob Fr agmentations Dan Tao Overman Group Meeting 9/24/12
2 What is a Grob Fragmentation? Heterolytic fragmentation is certain combinations of carbon and hetero atoms which undergo a regulated cleavage into three fragments. Electrofugal Fragment Unsaturated Fragment Nucleofugal Fragment Heteroatoms seen in the Grob Fragmentation include halogens, B, O, N, S, and P. Grob, C. A. Angew. Chem., Int. Ed. 1969, 8, 535.
3 Initial Discoveries Eschenmoser (1952) Grob (1955) Eschenmoser, A.; Frey, A. Helv. Chim. Acta 1952, 35, Grob, C. A.; Baumann, W. Helv. Chim. Acta 1955, 38, 594.
4 Mechanism and Side Reactions Grob fragmentations can proceed in either stepwise or concerted pathways, though the concerted pathway is typically preferred. Prantz, K.; Mulzer, J. Chem. Rev. 2010, 110, Kato, M.; Tooyama, Y.; Yoshikoshi, A. Bull. Chem. Soc. Jpn. 1991, 64, 50.
5 Effects of Nucleophiles/Bases Prantz, K.; Mulzer, J. Chem. Rev. 2010, 110, 3741.
6 Stereoelectronic Requirements For concerted Grob fragmentations, the centers must have anti-periplanar alignment for donation into antibonding orbitals Bottini, A. T.; Grob, C. A.; Schumacher, E.; Zergeny, J. Helv. Chim. Acta 1966, 49, Wharton, P. S.; Hiegel, G. A. Angew. Chem. Int. Ed. 1969, 8, 535.
7 Application in Synthesis: Ring Fragmentation Transformation of 1,3-alkyl substitution into carbonyl and alkene Zurflueh, R.; Wall, E. N.; Siddall, J. B.; Edwards, J. A. J. Am. Chem. Soc. 1968, 90, Peng, X.-S.; Wong, H. N. Chem. Asian J. 2006, 12, 111.
8 Application in Synthesis: Ring Expansion Larionov, O. V.; Corey, E. J. J. Am. Chem. Soc. 2008, 130, 2954.
9 Application in Synthesis: Ring Expansion Zhang, W.; Dowd, P. Tetrahedron Lett. 1996, 37, 957. Thorton, P. D.; Burnell, D. J. Org. Lett. 2006, 8, 3195.
10 Application in Synthesis: Ring Expansion Yoshimitsu, T.; Yanagiya, M.; Nagaoka, H. Tetrahedron Lett. 1999, 40, Maimone, T. J.; Shi, J.; Ashida, S.; Baran, P. S. J. Am. Chem. Soc. 2009, 131,
11 Grob-type Fragmentation Variations The Eschenmoser Tanabe Fragmentation (Fragmentation into alkynes) Eschenmoser, A.; Felix, D.; Ohloff, G. Helv. Chim. Acta 1967, 50, 708. Kamijo, S.; Dudley, G. B. J. Am. Chem. Soc. 2005, 127, 5028.
12 Grob-type Fragmentation Variations Fragmentation into allenes Transition metal-promoted fragmentation Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2010, 49, Mori, M.; Kimura, M.; Tanaka, S.; Tamaru, Y. Chem. Commun. 2006, 41, Kimura, M.; Masahiko, M.; Tamaru, Y. Chem. Commun. 2007, 43, 4504.
13 Enzymatic Catalysis Oxidosqualene cyclase (OSC) catalyzes Grob fragmentations of triterpene skeletons Shibuya, M.; et al. J. Am. Chem. Soc. 2007, 129, Hoshino, T.; Sato, T. Chem. Commun. 2002, 291.
14 Syn Grob Fragmentations Suprisingly, the endo epoxide is favored to undergo Grob fragmentation over the exo epoxide with anti-alignment The authors suggest that the C 1 -C 2 bond and the C 6 -O are more nearly coplanar in the endo epoxides Holton, R. A.; Kennedy, R. M. Tetrahedron Lett. 1984, 25, 4455.
15 SET-Induced Grob Fragmentations Some SET processes are able to undergo fragmentation in both the syn and anti configurations Hamura, T.; Suzuki, T.; Matsumoto, T.; Suzuki, K. Angew. Chem., Int. Ed. 2006, 45, Wender, P. A.; Manly, C. J. J. Am. Chem. Soc. 1990, 112, 8579.
16 Other Interesting Examples Decarboxylative Double Fragmentation Tandem Aldol/Grob Fragmentation Tandem Semipinacol Rearrangement/Grob Fragmentation Sternbach, D.; Jaisli, F.; Bonetti, M.; Eschenmoser, A.; Shibuya, M. Angew. Chem., Int. Ed. 1979, 18, 634. Kabalka, G. W.; Li, N. S. Tejedor, D.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1999, 64, Yuan, D.-Y.; Tu, Y.-Q.; Fan, C.-A. J. Org. Chem. 2008, 73, 7797.
17 Summary The Grob fragmentation is a useful reaction in synthesis -in obtaining functional handles from alkyl 1,3-diol species -in forming medium to large rings in steriocontrolled fashion Variations include use of transition metals, formation of alkynes or allenes, and radical-mediated processes The Grob fragmentation can be used in tandem with a variety of other processes such as the Aldol and Pinnacol reactions
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
STEREOELECTRONIC EFFECTS (S.E.) IN ORGANIC CHEMISTRY
STEREOELECTRONIC EFFECTS (S.E.) IN ORGANIC CHEMISTRY Pierre Deslongchamps (version du 16 février 2010) Cf. pour le livre: http://pages.usherbrooke.ca/pdeslongchamps/cv.htm 1 SECTION 8 Stereoelectronic
SECTION 3. Antiperiplanar Hypothesis. and Reactions at Unsaturated Systems
SECTION 3 Antiperiplanar Hypothesis and Reactions at Unsaturated Systems (2016) 1 Reaction on Sp 2 Type Unsaturated System In cyclic ketone, both processes lead to a chair but we will see that C-H and
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
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,
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
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.
Dyotropic Rearrangements. Presented by Matthew Burk
Dyotropic Rearrangements Presented by Matthew Burk 5-11-2010 What is a Dyotropic Rearrangement? A process in which two σ-bonds simultaneously migrate intramolecularly Type 1 2 σ bonds exchange their positions
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
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
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
Synthesis of Cyclobutanone and Cyclobutenone
Synthesis of Cyclobutanone and Cyclobutenone Salan, J., in Science of Synthesis, 26 (2004),p.557 Ruben Martin, Synthesis, 2013, 45, 563 Penghao Chen Dong Group Seminar Aug, 22 nd, 2013 Synthetic Application
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
REARRANGEMENTS NOTES Mechanistic Aspects of Rearrangements
- 1 - REARRANGEMENTS NOTES Mechanistic Aspects of Rearrangements Nature of the Rearrangement It can vary from being truly stepwise to migration occurring in concert with initial ionisation. These two situations
Citation HETEROCYCLES, 82(1), pp ; 20. Issue Date
NASITE: Nagasaki University's Ac Title Decarboxylative C-C Bond Cleavage Author(s) Kimura, Masanari; Kohno, Tomohiko; Citation HETECYCLES, 82(), pp.28-287; 20 Issue Date 200 UL http://hdl.handle.net/0069/24975
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
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals. Phil Knutson Ferreira Group 12/3/2015
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals Phil Knutson Ferreira Group 12/3/2015 New strategies in organic synthesis nsf-cchf.com What
SYNTHESIS OF ALKENES BY FRAGMENTATION REACTIONS; MECHANISTIC VIEWS; THE ORGANIC CHEMISTRY NOTEBOOK SERIES, A DIDACTICAL APPROACH, Nº 5
REVISTA BLIVIANA DE QUÍMICA Vol., No., pp. -, May./Jun. 0 Bolivian Journal of Chemistry () -, May/Jun. 0 Received 0 0 0 Accepted 0 0 Published 0 0 0 SYNTESIS F ALKENES BY FRAGMENTATIN REACTINS; MECANISTIC
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
Conjugated Systems, Orbital Symmetry and UV Spectroscopy
Conjugated Systems, Orbital Symmetry and UV Spectroscopy Introduction There are several possible arrangements for a molecule which contains two double bonds (diene): Isolated: (two or more single bonds
Chemistry III (Organic): An Introduction to Reaction Stereoelectronics. LECTURE 6 1,2-Rearrangements & Fragmantations
1 Chemistry III (rganic): An Introduction to Reaction Stereoelectronics LECTURE 6 1,2-Rearrangements & Fragmantations Alan C. Spivey a.c.spivey@imperial.ac.uk Nov 2015 2 Format & scope of lecture 6 Ionic
Rhenium-Catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single-Bond Cleavage
henium-catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single-Bond Cleavage Kuninobu, Y.; Takata,.; Kawata, A.; Takai, K. rg. Lett. ASAP Et 5 6 cat. [ebr(c) 3 (thf)] 2 5 6 Current Literature
Ynolate Chemistry. Jeff Kallemeyn October 22, 2002
Ynolate Chemistry While enolates have numbered among the most important reagents of organic chemistry for more than a century, ynolates have hitherto remained unknown although their chemistry should be
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,
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-
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
Synthesis, Mechanism, and Properties of Cyclopenta-fused Polycyclic Aromatic Hydrocarbons. Chaolumen. Introduction
March 22, 2018 Synthesis, Mechanism, and Properties of Cyclopenta-fused Polycyclic Aromatic Hydrocarbons Reaxys Prize Club Symposium in Japan 2018 Chaolumen Institute for Chemical Research, Kyoto University
Dehydrohalogenation of Alkyl Halides E2 and E1 Reactions in Detail
Dehydrohalogenation of Alkyl Halides E2 and E1 Reactions in Detail b-elimination Reactions Overview dehydration of alcohols: X = H; Y = OH dehydrohalogenation of alkyl halides: X = H; Y = Br, etc. X C
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
Ethers. Chapter 14: Ethers, Epoxides, & Sulfides. General Formula: Types: a) Symmetrical: Examples: b) Unsymmetrical: Examples: Physical Properties:
Chamras Chemistry 106 Lecture Notes Examination 1 Materials Chapter 14: Ethers, Epoxides, & Sulfides Ethers General Formula: Types: a) Symmetrical: Examples: b) Unsymmetrical: Examples: Physical Properties:
Organic Molecules, Photoredox, and. Catalysis
Organic Molecules, Photoredox, and Catalysis 1 What is Photoredox Catalysis 2 Transition Metal vs Organic Photoredox Transition Metal Catalysts Organic Catalyst Reprinted (2017) with permission from (Wangelin,
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:
Aza-Wacker-Type Cyclization. Group Meeting Tuesday, April 19, 2011 William Kuester
Aza-Wacker-Type Cyclization Group Meeting Tuesday, April 19, 2011 William Kuester N-heterocylization Reductive Amination Hydroamination Oxidative Cyclization Chemler, S.R. Org. Biomol. Chem. 2009, 7, 3009-3019.
Discussion Addendum for: Nickel-catalyzed Homoallylation of Aldehydes with 1,3-Dienes
DI:10.15227/orgsyn.090.0105 Discussion Addendum for: Nickel-catalyzed Homoallylation of Aldehydes with 1,3-Dienes CH anti:syn = 30:1 CH cat. Et 2 Zn anti:syn = 30:1 Prepared by Masanari Kimura.* 1 riginal
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
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
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,
Chapter 7 - Alkenes and Alkynes I
Andrew Rosen Chapter 7 - Alkenes and Alkynes I 7.1 - Introduction - The simplest member of the alkenes has the common name of ethylene while the simplest member of the alkyne family has the common name
Modern Synthetic Methods
Modern Synthetic Methods Dr. Dorian Didier dodich@cup.uni-muenchen.de Functionnalized Organometallic Reagents C-N, C-O and C-S Bond Formation Introduction to Organoboron Chemistry Introduction to Organosilicon
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,
CH 3 TMG, DMF N H 3 CO 2 S. (PPh 3 ) 2 Pd 0
1. (a) rovide a reasonable mechanism for the following transformation. I S 2 C 3 C 3 ( 3 ) 2 2, CuI C 3 TMG, DMF 3 C 2 S TMG = Me 2 Me 2 ICu ( 3 ) 2 0 I S 2 C 3 S 2 C 3 Cu I 3 3 3 C 2 S I 3 3 3 C 2 S 3
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.
REACTION AND SYNTHESIS REVIEW
REACTION AND SYNTHESIS REVIEW A STUDENT SHOULD BE ABLE TO PREDICT PRODUCTS, IDENTIFY REACTANTS, GIVE REACTION CONDITIONS, PROPOSE SYNTHESES, AND PROPOSE MECHANISMS (AS LISTED BELOW). REVIEW THE MECHANISM
New bond. ph 4.0. Fischer esterification. New bond 2 O * New bond. New bond H 2N. New C-C bond. New C-C bond. New C-C bond. O Cl.
Iverson C 0N KRE Table: For use in synthesis problems, count carbons in products and starting materials then identify location(s) of new s, especially C-C or C=C s. With that information, use the following
Organic Chemistry Lecture 2 - Hydrocarbons, Alcohols, Substitutions
ALKANES Water-insoluble, low density C-C single bonds Higher MW -> higher BP, higher MP Branching -> lower BP, higher MP Forms cycloalkanes which can have ring strain Cyclohexane: chair vs. boat configuration
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
Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products*
Pure Appl. Chem., Vol. 85, No. 4, pp. 741 753, 2013. http://dx.doi.org/10.1351/pac-con-12-10-01 2013 IUPAC, Publication date (Web): 13 March 2013 Aziridinyl imines in organic synthesis: Development of
JEFFERSON COLLEGE COURSE SYLLABUS CHM200 ORGANIC CHEMISTRY I. 5 Credit Hours. Prepared by: Richard A. Pierce
JEFFERSON COLLEGE COURSE SYLLABUS CHM200 ORGANIC CHEMISTRY I 5 Credit Hours Prepared by: Richard A. Pierce Revised Date: January 2008 by Ryan H. Groeneman Arts & Science Education Dr. Mindy Selsor, Dean
TMSCl imidazole DMF. Ph Ph OTMS. Michael reaction. Michael reaction Ph R 3. epoxidation O R
eaction using diarylprolinol silyl ether derivatives as catalyst 1) C Et K C 3, ) MgBr, TF TMS hexane, 0 o C TBS p- C 6 4, T C Et 85%, 99% ee Angew. Chem., nt. Ed., 44, 41 (005). rg. Synth., 017, 94, 5.
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
Metalloporphyrin. ~as efficient Lewis acid catalysts with a unique reaction-field~ and. ~Synthetic study toward complex metalloporphyrins~
Metalloporphyrin ~as efficient Lewis acid catalysts with a unique reaction-field~ and ~Synthetic study toward complex metalloporphyrins~ Literature Seminar Kenta Saito (D1) 1 Topics Chapter 1 ~as efficient
1.13 Acid-Base Reactions: Lone-Pair Donors & Acceptors
1.13 Acid-Base Reactions: Lone-Pair Donors & Acceptors I, Cl, N 3, 3 P 4 pka 10 to 5 Super strong acids 3 + pka 1.7 RC 2 pka ~ 5 acids Ph pka ~ 10 get 2, R pka ~ 16 weaker RCC (alkynes) pka ~ 26 RN 2 pka
OChem 1 Mechanism Flashcards. Dr. Peter Norris, 2018
OChem 1 Mechanism Flashcards Dr. Peter Norris, 2018 Mechanism Basics Chemical change involves bonds forming and breaking; a mechanism describes those changes using curved arrows to describe the electrons
OChem 1 Mechanism Flashcards. Dr. Peter Norris, 2015
OChem 1 Mechanism Flashcards Dr. Peter Norris, 2015 Mechanism Basics Chemical change involves bonds forming and breaking; a mechanism describes those changes using curved arrows to describe the electrons
ORGANIC - BROWN 8E CH ALKENES AND REACTIONS OF ALKENES
!! www.clutchprep.com CONCEPT: ALKENES and ALKYNES Alkenes/Alkynes are named by adding the suffix modifier (- /- ) to the end of the root. Alkenes/alkynes receive in numbering alkanes Location is assigned
The Total Synthesis of Vitamin B12
The Total Synthesis of Vitamin B12 The most advanced synthetic intermediate as of 1968 Nathan S. Werner Denmark Group Meeting September 28 th, 2010 Biology of Vitamin B 12 Vitamin B 12, common name cobalamin,
σ Bonded ligands: Transition Metal Alkyls and Hydrides
σ Bonded ligands: Transition Metal Alkyls and Hydrides Simplest of organo-transitionmetal species Rare until and understanding of their stability in the 60 s and 70 s Metal alkyls can be considered as
Titanacyclopropanes as versatile intermediates for carbon carbon bond formation in reactions with unsaturated compounds*
Pure Appl. Chem., Vol. 72, No. 9, pp. 1715 1719, 2000. 2000 IUPAC Titanacyclopropanes as versatile intermediates for carbon carbon bond formation in reactions with unsaturated compounds* O. G. Kulinkovich
Suggested solutions for Chapter 40
s for Chapter 40 40 PBLEM 1 Suggest mechanisms for these reactions, explaining the role of palladium in the first step. Ac Et Et BS () 4 2 1. 2. K 2 C 3 evision of enol ethers and bromination, the Wittig
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.
FORBIDDEN 1,2-CARBANION SHIFTS MECHANISM AND APPLICATION OF THE FRITSCH- BUTTENBERG-WIECHELL REARRANGEMENT. Chun Ho Lam
1 FORBIDDEN 1,2-CARBANION SHIFTS MECHANISM AND APPLICATION OF THE FRITSCH- BUTTENBERG-WIECHELL REARRANGEMENT Chun Ho Lam 17 th November 2010 Chun Ho Lam 17 th November, 2010 Contents 2 Section 1: Discovery
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
ORGANIC CHEMISTRY. Chapter Cycloalkenes. Department of Chemistry, Xiamen University
ORGANI EMISTRY hapter 7 7.4 ycloalkenes Department of hemistry, Xiamen University ORGANI EMISTRY hapter 7 The rings of cycloalkenes containing five carbon atoms or fewer exist only in the cis form. yclopropene
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
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
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
-catalyzed reactions utilizing isocyanides as a C 1
Pure Appl. Chem., Vol. 78, No. 2, pp. 275 280, 2006. doi:10.1351/pac200678020275 2006 IUPAC GaCl 3 -catalyzed reactions utilizing isocyanides as a C 1 source* Mamoru Tobisu, Masayuki Oshita, Sachiko Yoshioka,
Literature Report 2. Stereocontrolled Synthesis of Kalihinol C. Reiher, C. A.; Shenvi, R. A. J. Am. Chem. Soc. 2017, 139,
Literature Report 2 Stereocontrolled Synthesis of Kalihinol C Reporter: Huanping Xie Checker: Xiang Gao Date: 2017-04-17 Reiher, C. A.; Shenvi, R. A. J. Am. Chem. Soc. 2017, 139, 3647 3650. Contents 1
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
Nuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320
Nuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320 I. Isolated, cumulated, and conjugated dienes A diene is any compound with two or C=C's is a diene. Compounds containing more than two
Domino processes for the synthesis of N-vinylazoles starting from vinyl selenones
The 18 th International Electronic Conference on Synthetic Organic Chemistry Domino processes for the synthesis of N-vinylazoles starting from vinyl selenones 1. Introduction Martina Palomba, Francesca
Chapter 7 Alkenes and Alkynes I: Properties and Synthesis Elimination Reactions of Alkyl Halides"
Chapter 7 Alkenes and Alkynes I: Properties and Synthesis Elimination Reactions of Alkyl Halides The (E)-(Z) System for Designating Alkene Diastereomers The Cahn-Ingold-Prelog convention is used to assign
Dr. P. Wipf Chem /26/2007
I. Basic Principles I-L. Radicals & Carbenes Features of Radical Reactions Review: Curran, D. P. In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Ed.; Pergamon Press: Oxford, 1991; Vol.
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
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
Friedel-Crafts. (Professor Peter J. Stang)
Friedel-Crafts (Professor Peter J. Stang) (1) S. Saito and Y. Koizumi, Copper-catalyzed coupling of aryl halides and nitrite salts: a mild Ullmann-type synthesis of aromatic nitro compounds Tetrahedron
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,
ELECTROPHILIC ADDITIONS OF ALKENES AS THE COUNTERPART OF ELIMINATIONS
ELECTRPHILIC ADDITINS F ALKENES AS THE CUNTERPART F ELIMINATINS INTRDUCTIN - Chapter 8 is mostly about alkene reactions. That is, how one can transform alkenes into other functional groups. Most of these
Selectivity and Natural Product Synthesis. Reporter: Liang Xin-ting Supervisors: Prof. Yang Prof. Chen Prof. Tang
Selectivity and Natural Product Synthesis Reporter: Liang Xin-ting Supervisors: Prof. Yang Prof. Chen Prof. Tang Content Introduction Selectivity of oxidative coupling Chemoselectivity Regioselectivity
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
Ethers can be symmetrical or not:
Chapter 14: Ethers, Epoxides, and Sulfides 175 Physical Properties Ethers can be symmetrical or not: linear or cyclic. Ethers are inert and make excellent solvents for organic reactions. Epoxides are very
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
Problem session (3) Daiki Kuwana. Please fill in the blank and explain reaction mechanisms and stereoselectivities.
Problem session (3) Daiki Kuwana Please fill in the blank and explain reaction mechanisms and stereoselectivities. 1. 1-1 1. (Ac) 2 (10 mol%), DPEphos (20 mol%) Et 3, toluene, 90 C 2. s 4 (14 mol%), M;
Conjugated Systems. With conjugated double bonds resonance structures can be drawn
Conjugated Systems Double bonds in conjugation behave differently than isolated double bonds With conjugated double bonds resonance structures can be drawn With isolated double bonds cannot draw resonance
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,
CHEMISTRY 231 GENERAL ORGANIC CHEMISTRY I FALL 2014 List of Topics / Examination Schedule
Page 1 of 5 CHEMISTRY 231 FALL 2014 List of Topics / Examination Schedule Unit Starts Topic of Study 20 Aug 2014 STRUCTURE AND BONDING Suggested Reading: Chapter 1 29 Aug 2014 ALKANES & CYCLOALKANES Suggested
Alcohol Synthesis. Dr. Sapna Gupta
Alcohol Synthesis Dr. Sapna Gupta Synthesis of Alcohols Alcohols can be synthesized from several functional groups. Nucleophilic substitution of O - on alkyl halide ydration of alkenes water in acid solution
Metal Hydrides, Alkyls, Aryls, and their Reactions
Metal Hydrides, Alkyls, Aryls, and their Reactions A Primer on MO Theory σ-bonding in Organotransition Metal Complexes M-C Bond Energies in Organotransition Metal Complexes Thermodynamic Predictions
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
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
[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
Module 10 : Reaction mechanism. Lecture 1 : Oxidative addition and Reductive elimination. Objectives. In this lecture you will learn the following
Module 10 : Reaction mechanism Lecture 1 : Oxidative addition and Reductive elimination Objectives In this lecture you will learn the following The oxidative addition reactions. The reductive elimination
Transition-metal-catalyzed multicomponent coupling reactions with imines and carbon monoxide*
Pure Appl. Chem., Vol. 85, No. 2, pp. 377 384, 2013. http://dx.doi.org/10.1351/pac-con-12-10-15 2013 IUPAC, Publication date (Web): 21 January 2013 Transition-metal-catalyzed multicomponent coupling reactions
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
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
Research in our group encompasses the following 4 areas in Synthetic Organic Chemistry.
Research in our group encompasses the following 4 areas in Synthetic Organic Chemistry. 1] Development of Asymmetric Catalysis 2] Total Synthesis of Natural products 3] Development of Novel Protecting-Group-Free
Only five of the molecules below may be prepared as the sole product of allylic halogenation of the respective alkene. Circle those five.
Chem 232 D. J. Wardrop wardropd@uic.edu Problem Set 6 Answers Question 1. nly five of the molecules below may be prepared as the sole product of allylic halogenation of the respective alkene. Circle those
Chapter 13 Conjugated Unsaturated Systems
Chapter 13 Conjugated Unsaturated Systems Introduction Conjugated unsaturated systems have a p orbital on a carbon adjacent to a double bond The p orbital can come from another double or triple bond The
π-alkyne metal complex and vinylidene metal complex in organic synthesis
Literature Seminar 080220 Kenzo YAMATSUGU (D1) π-alkyne metal complex and vinylidene metal complex in organic synthesis 0. Introduction ' ' = π-alkyne metal complex vinylidene metal complex ecently, electrophilic
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