Nickel-catalyzed multi-component connection reaction of isoprene, aldimines (lactamines), and diphenylzinc
作者:Keisuke Kojima、Masanari Kimura、Satoshi Ueda、Yoshinao Tamaru
DOI:10.1016/j.tet.2006.03.116
日期:2006.8
Ni(acac)2 catalyzes the four-component connection reaction of diphenylzinc, isoprene, aromatic aldehydes, and aromatic amines in this order and provides stereochemically homogeneous (E)-1-arylamino-1-aryl-3-methyl-5-phenyl-3-pentenes (1) in excellent yields. Aliphatic aldehydes react similarly and give (E)-1-arylamino-1-alkyl-3-methyl-5-phenyl-3-pentenes (1) in slightly reduced yields. When the alkyl groups are bulky, in addition to I are formed (E)-1-arylamino-1-alkyl-4-methyl-5-phenyl-3-pentenes (F) as the minor products. Lactamines prepared in situ from five- and six-membered lactols and aromatic amines are more reactive than alkyl aldehyde aldimines and furnish (E)-4-arylamino-6-methyl-8-phenyl-6-octen-1-ols (4) and (E)-5-arylamino-7-methyl-9-phenyl-7-nonen-1-ols (5), respectively, in good yields with excellent E-stereoselectivity. (c) 2006 Elsevier Ltd. All rights reserved.