Highly enantioselective aldol reaction of acetone with β,γ-unsaturated α-keto esters promoted by simple chiral primary-tertiary diamine catalysts

Lin Peng; Liang-Liang Wang; Jian-Fei Bai; Li-Na Jia; Yun-Long Guo; Xi-Ya Luo; Fei-Ying Wang; Xiao-Ying Xu; Li-Xin Wang

doi:10.1039/c1ob05607g

Highly enantioselective aldol reaction of acetone with β,γ-unsaturated α-keto esters promoted by simple chiral primary-tertiary diamine catalysts

Org Biomol Chem. 2011 Jul 7;9(13):4774-7. doi: 10.1039/c1ob05607g. Epub 2011 May 26.

Authors

Lin Peng¹, Liang-Liang Wang, Jian-Fei Bai, Li-Na Jia, Yun-Long Guo, Xi-Ya Luo, Fei-Ying Wang, Xiao-Ying Xu, Li-Xin Wang

Affiliation

¹ Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.

PMID: 21614388
DOI: 10.1039/c1ob05607g

Abstract

A series of primary-tertiary diamine catalysts were successfully applied to promote the enantioselective aldol reaction of acetone with β,γ-unsaturated α-keto esters in excellent yields (up to 99%) and enantioselectivities (up to 96% ee).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetone / chemistry*
Aldehydes / chemistry
Catalysis
Diamines / chemistry*
Esters / chemistry*
Molecular Structure
Stereoisomerism

Substances

Aldehydes
Diamines
Esters
Acetone
3-hydroxybutanal