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Synfacts 2011(11): 1242-1242  
DOI: 10.1055/s-0031-1289267
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Desymmetrization of Cyclohexadienones via Cinchonine-Derived Thiourea

Contributor(s): Benjamin List, Qinggang Wang
Q. Gu, S.-L. You*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

You and co-workers have developed a protocol for the desymmetrization of ­cyclohexadienones via an aza-Michael reaction catalyzed by cinchonine-derived thiourea 1. This reaction affords a series of highly enantioenriched pyrrolidine and morpholine derivatives in excellent yields and enantioselectivities. With this methodology, an enantioselective total synthesis of (-)-mesembrine has been accomplished.