title: beta-Isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines.
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.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
authors.forename: Sakie
authors.initials: S
authors.lastname: Kawahara
authors.forename: Ayako
authors.initials: A
authors.lastname: Nakano
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Esumi
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
authors.forename: Susumi
authors.initials: S
authors.lastname: Hatakeyama