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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)

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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.

Key words

primary amines - N-heterocycles - enones - conjugate addition - catalysis

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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.