Literature DB >> 15311954

Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents.

Benjamin List1.   

Abstract

The chemistry of preformed enamines, especially their use as enolate equivalents, has been a well-investigated area of research since the early 1950s. However, enamine catalysis, the catalysis of carbonyl transformations via enamine intermediates by using primary and secondary amines as catalysts, has only been fully appreciated as a powerful strategy for asymmetric synthesis since the beginning of this century. Contributions from this laboratory to the revitalized interest in asymmetric enamine catalysis are summarized in this Account.

Entities:  

Year:  2004        PMID: 15311954     DOI: 10.1021/ar0300571

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  35 in total

Review 1.  The direct catalytic asymmetric aldol reaction.

Authors:  Barry M Trost; Cheyenne S Brindle
Journal:  Chem Soc Rev       Date:  2010-02-17       Impact factor: 54.564

2.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

3.  Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators.

Authors:  Henrik Sundén; Linda Ta; Anton Axelsson
Journal:  J Vis Exp       Date:  2015-11-27       Impact factor: 1.355

4.  Synthesis of Oxazolidinone and Tosyl Enamines by Tertiary Amine Catalysis.

Authors:  Nicholas A Eddy; Peter D Morse; Martha D Morton; Gabriel Fenteany
Journal:  Synlett       Date:  2011-01-01       Impact factor: 2.454

5.  An efficient three-component synthesis of highly functionalized tetrahydroacenaphtho[1,2-b]indolone derivatives catalyzed by L-proline.

Authors:  Juan-Juan Zhang; Xian Feng; Xue-Cheng Liu; Zhi-Bin Huang; Da-Qing Shi
Journal:  Mol Divers       Date:  2014-08-24       Impact factor: 2.943

6.  Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones.

Authors:  Qunsheng Guo; Mayur Bhanushali; Cong-Gui Zhao
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

7.  A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes.

Authors:  Eric M Phillips; Manabu Wadamoto; Audrey Chan; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  N-heterocyclic carbene-catalyzed enantioselective Mannich reactions with alpha-aryloxyacetaldehydes.

Authors:  Yasufumi Kawanaka; Eric M Phillips; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

9.  Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.

Authors:  Sampak Samanta; Sandun Perera; Cong-Gui Zhao
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

10.  Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Authors:  Qiang Sha; Hadi Arman; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222

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