Literature DB >> 15311957

Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-alder reactions.

Wolfgang Notz1, Fujie Tanaka, Carlos F Barbas.   

Abstract

Enamines and imines have long been recognized as key intermediates in enzyme catalysis, particularly within a class of enzymes organic chemists would very much like to emulate, the aldolases. Here we summarize the contributions of this laboratory to converting enzymatic enamines, and in some cases imines, into a versatile catalytic asymmetric strategy powered by small organic molecules.

Entities:  

Year:  2004        PMID: 15311957     DOI: 10.1021/ar0300468

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


  71 in total

1.  Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors:  Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal:  Aldrichimica Acta       Date:  2008       Impact factor: 3.667

Review 2.  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

3.  Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts.

Authors:  Hong Xu; Jia Gao; Donglin Jiang
Journal:  Nat Chem       Date:  2015-09-21       Impact factor: 24.427

4.  Solid-Phase Synthesis of β-Amino Ketones Via DNA-Compatible Organocatalytic Mannich Reactions.

Authors:  Nam Tran-Hoang; Thomas Kodadek
Journal:  ACS Comb Sci       Date:  2018-01-24       Impact factor: 3.784

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.  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

8.  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

9.  Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

10.  Direct observation of an enamine intermediate in amine catalysis.

Authors:  Xueyong Zhu; Fujie Tanaka; Richard A Lerner; Carlos F Barbas; Ian A Wilson
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419

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