期刊
TETRAHEDRON
卷 62, 期 49, 页码 11499-11505出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.07.071
关键词
cinchona alkaloids; thiourea; organic catalysis; imines; Mannich reaction; Aza-Henry reaction
Cinchona alkaloid-derived thiourea catalysts promote nucleophilic additions to acyl imines for the asymmetric synthesis of secondary amine adducts. The hydroquinine-derived thiourea catalyst efficiently promotes the aza-Henry reaction of nitroalkane with acyl imines, affording beta-nitroamines in good yields with enantioselectivities of 90-98% ee and diastereoselectivities up to 97%. The scope of the reaction also includes dimethyl malonate as a nucleophile to access beta-amino esters in high enantiopurity. Under the optimized reaction conditions, secondary amine adducts of high enantiopurity are generated based on various aromatic and alpha, beta-unsaturated acyl imines. (c) 2006 Elsevier Ltd. All rights reserved.
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