Enantioselective organocatalytic tandem Michael-Aldol reactions: one-pot synthesis of chiral thiochromenes

Wei Wang; Hao Li; Jian Wang; Liansuo Zu

doi:10.1021/ja063328m

Enantioselective organocatalytic tandem Michael-Aldol reactions: one-pot synthesis of chiral thiochromenes

J Am Chem Soc. 2006 Aug 16;128(32):10354-5. doi: 10.1021/ja063328m.

Authors

Wei Wang¹, Hao Li, Jian Wang, Liansuo Zu

Affiliation

¹ Department of Chemistry, University of New Mexico, Albuquerque, New Mexico 87131-0001, USA. wwang@unm.edu

PMID: 16895386
DOI: 10.1021/ja063328m

Abstract

A highly enantioselective (S) diphenylpyrrolinol silyl ether promoted tandem Michael-aldol reaction of alpha,beta-unsaturated aldehydes with 2-mercaptobenzaldehydes has been developed. The method affords one-pot access to chiral and synthetically useful thiochromenes in high yields and high enantioselectivities from readily available compounds.

Publication types

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

MeSH terms

Benzopyrans / chemical synthesis*
Benzopyrans / chemistry
Catalysis
Chemistry, Organic / methods*
Molecular Structure
Stereoisomerism
Sulfur Compounds / chemistry*

Substances

Benzopyrans
Sulfur Compounds