Literature DB >> 11777477

Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde.

Armando Córdova1, Wolfgang Notz, Carlos F Barbas.   

Abstract

For the first time, the L-proline-catalyzed direct asymmetric self-aldolization of acetaldehyde is described affording (+)-(5S)-hydroxy-(2E)-hexenal 2 with ee's ranging from 57 to 90%. Further transformations of 2 into synthetically valuable building blocks are presented. A mechanism for the formation of 2 is proposed.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 11777477     DOI： 10.1021/jo015881m

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  New mechanistic studies on the proline-catalyzed aldol reaction.

Authors:  Benjamin List; Linh Hoang; Harry J Martin
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-08       Impact factor: 11.205

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.  The peptide-catalyzed stereospecific synthesis of tetroses: a possible model for prebiotic molecular evolution.

Authors:  Arthur L Weber; Sandra Pizzarello
Journal:  Proc Natl Acad Sci U S A       Date:  2006-08-11       Impact factor: 11.205

4.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors:  Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

5.  Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.

Authors:  Yonggui Chi; Li Guo; Nathan A Kopf; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2008-04-04       Impact factor: 15.419

6.  Enantioselective direct aldol reactions catalyzed by L-prolinamide derivatives.

Authors:  Zhuo Tang; Fan Jiang; Xin Cui; Liu-Zhu Gong; Ai-Qiao Mi; Yao-Zhong Jiang; Yun-Dong Wu
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-12       Impact factor: 11.205

7.  Chiral phosphoramide-catalyzed, enantioselective, directed cross-aldol reactions of aldehydes.

Authors:  Scott E Denmark; Tommy Bui
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

8.  Proline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: an experimental and theoretical study.

Authors:  Nevin Arslan; Selami Ercan; Necmettin PİrİnÇÇİoĞlu
Journal:  Turk J Chem       Date:  2020-04-01       Impact factor: 1.239

9.  The Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate.

Authors:  Weiqiang Chen; Huaquan Fang; Kaixue Xie; Martin Oestreich
Journal:  Chemistry       Date:  2020-10-22       Impact factor: 5.236
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.