Synthesis 2009(9): 1564-1572  
DOI: 10.1055/s-0029-1216636
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Conjugate Addition of N-Heterocycles to α,β-Unsaturated Ketones Catalyzed by Chiral Primary Amines

Guangshun Luoa, Shilei Zhanga, Wenhu Duan*a,b, Wei Wang*a,c
a Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. of China
b Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences, Graduate School of the Chinese Academy of Sciences, Shanghai 201203, P. R. of China
c Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131-0001, USA
Fax: +1(505)2772609; e-Mail: wwang@unm.edu;
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Publikationsverlauf

Received 29 January 2009
Publikationsdatum:
14. April 2009 (online)

Abstract

A new organocatalytic enantioselective conjugate addition reaction of nitrogen-centered heterocycles with α,β-unsaturated ketones has been developed. Promoted by a chiral cinchona alkaloid derived primary amine, the reaction affords the adducts in moderate to high enantioselectivities.

13

Determined by measurement of the optical rotations of the known compounds and comparison with those reported in the literature; see refs. 5e and 9b.