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β-Isocupreidine-Catalyzed Asymmetric Baylis−Hillman Reaction of Imines

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journal contribution
posted on 2003-08-02, 00:00 authored by Sakie Kawahara, Ayako Nakano, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama
β-Isocupreidine (β-ICD)-catalyzed asymmetric Baylis−Hillman reactions of aromatic imines with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-α-methylene-β-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.

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