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Synfacts 2006(10): 1065-1065
DOI: 10.1055/s-2006-949371
DOI: 10.1055/s-2006-949371
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Organocatalytic One-Pot Synthesis of Chiral Thiochromenes
H. Li, J. Wang, L. Zu, W. Wang*
University of New Mexico, Albuquerque, USA
Further Information
Publication History
Publication Date:
21 September 2006 (online)
Significance
Here the authors report an enantioselective tandem-Michael-aldol reaction between α,β-unsaturated aldehydes and thiophenol aldehydes leading to an efficient synthesis of chiral thiochromenes. (S)-Pyrrolidine silyl ether 1 in combination with PhCO2H has been found to be effective for the reaction. With 10 mol% of catalyst 1 good to high yields (72-97%) and enantioselectivities (er = 93:7 to 98:2) are obtained for different aromatic and aliphatic α,β-unsaturated aldehydes.