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