Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 11, Pages 2073-2083Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901227
Keywords
Asymmetric catalysis; Organocatalysis; Nitrogen heterocycles; aza-Michael addition
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Funding
- National Natural Science Foundation of China [20672061]
- Chinese 863 Project [2007AA05Z102]
- Chinese 973 Program [2010CB833301]
- Nankai University State Key Laboratory of Elemento-Organic Chemistry
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A procedure for enantioselective organocatalytic conjugate additions of a variety of N-heterocycles to alpha,beta-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 1H-benzotriazole (1a) or 5-phenyltetrazole derivatives 12, providing the Michael addition products in high yields and with good to excellent enantioselectivities.
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