beta-Isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines.
作者信息
Kawahara Sakie, Nakano Ayako, Esumi Tomoyuki, Iwabuchi Yoshiharu, Hatakeyama Susumi
机构信息
Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
出版信息
Org Lett. 2003 Aug 21;5(17):3103-5. doi: 10.1021/ol035102j.
PMID:12916992
Abstract
[reaction: see text] beta-Isocupreidine (beta-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-alpha-methylene-beta-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.
摘要
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