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Synthesis 2009(9): 1564-1572
DOI: 10.1055/s-0029-1216636
DOI: 10.1055/s-0029-1216636
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New YorkEnantioselective Conjugate Addition of N-Heterocycles to α,β-Unsaturated Ketones Catalyzed by Chiral Primary Amines
Weitere Informationen
Received
29 January 2009
Publikationsdatum:
14. April 2009 (online)
Publikationsverlauf
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.
Key words
primary amines - N-heterocycles - enones - conjugate addition - catalysis
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Determined by measurement of the optical rotations of the known compounds and comparison with those reported in the literature; see refs. 5e and 9b.