Synfacts 2007(6): 0653-0653  
DOI: 10.1055/s-2007-968567
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Organocatalytic Domino Michael-Michael Addition Reactions

Contributor(s): Benjamin List, Nolwenn J. A. Martin
H. Li, L. Zu, H. Xie, J. Wang, W. Jiang, W. Wang*
University of New Mexico, Albuquerque, USA
Further Information

Publication History

Publication Date:
22 May 2007 (online)

Significance

The authors developed an efficient, asymmetric organocatalytic domino Michael-Michael addition reaction of α,β-unsaturated aldehydes 1 with trans-ethyl-4-mercapto-2-butenoate (2) in the presence of (S)-diphenylprolinol TMS ether (3). The reaction worked well with aromatic (bearing neutral, electron-donating or electron-withdrawing groups), heteroaromatic, and aliphatic α,β-unsaturated aldehydes 1 and provided chiral tetrahydrothiophenes 4 containing three stereogenic centers in good to excellent enantio­selectivities and high diastereoselectivities.