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Desymmetrization of cyclohexadienones viacinchonine derived thiourea-catalyzed enantioselective aza-Michael reaction and total synthesis of (-)-Mesembrine?

Chemical Science Pub Date: 2011-05-19 DOI: 10.1039/C1SC00083G

Abstract

Desymmetrization of cyclohexadienones via aza-Michael reaction catalyzed by cinchonine derived thiourea has been realized to afford a series of highly enantioenriched pyrrolidine and morpholine derivatives in excellent yields and ees. With this newly established methodology, asymmetric total synthesis of (-)-Mesembrine in high enantiomeric excess (98% ee) was accomplished.

Graphical abstract: Desymmetrization of cyclohexadienones viacinchonine derived thiourea-catalyzed enantioselective aza-Michael reaction and total synthesis of (-)-Mesembrine

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Chemical Science

Journal Name：Chemical Science

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