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Synlett 2012(2): 314-316  
DOI: 10.1055/s-0031-1290113
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Protonation in the Sulfa-Michael Addition Using Chiral Squaramides as Hydrogen-Bonding Organocatalysts

Le Dai, Hongjun Yang, Jingze Niu, Fener Chen*
Fudan-DSM Joint Lab for Synthetic Method and Chiral Technology, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
Fax: +86(21)65643811; e-Mail: rfchen@fudan.edu.cn;
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Publication History

Received 26 September 2011
Publication Date:
13 December 2011 (online)

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Abstract

An enantioselective protonation of transient enolate generated in sulfa-Michael addition was investigated. Various α-substituted acrylic derivatives and thiols were examined as substrates. α-Benzyl acrylimide gave the best results in terms of chemical yield and enantioselectivity (up to 93% yield and 92% ee)

Key words

asymmetric protonation - enantioselective catalysis - squaramide - hydrogen bonding

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