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beta-Isocupreidine-catalyzed Asymmetric Baylis-Hillman Reaction of Imines

Sakie Kawahara, Ayako Nakano, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama

Org Lett. 2003 Aug 21;5(17):3103-5.

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP2160896 1,1,1,3,3,3-Hexafluoroisopropyl acrylate 1,1,1,3,3,3-Hexafluoroisopropyl acrylate 2160-89-6 Price
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