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Organocatalytic Enantioselective aza‐Michael Additions of N‐Heterocycles to α,β‐Unsaturated Enones
Author(s) -
Lv Jian,
Wu Hao,
Wang Yongmei
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901227
Subject(s) - enantioselective synthesis , chemistry , michael reaction , enone , conjugate , organocatalysis , addition reaction , organic chemistry , catalysis , combinatorial chemistry , mathematical analysis , mathematics
A procedure for enantioselective organocatalytic conjugate additions of a variety of N‐heterocycles to α,β‐unsaturated enone systems is presented. The reactions are efficiently catalyzed by salts of 9‐amino‐9‐deoxy‐epiquinine ( 3d ). Cyclic, acyclic, and aromatic enones can be used in reactions with 1 H ‐benzotriazole ( 1a ) or 5‐phenyltetrazole derivatives 12 , providing the Michael addition products in high yields and with good to excellent enantioselectivities.