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

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 mec...

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Bibliographic Details
Published in:Organic letters 2003-08, Vol.5 (17), p.3103-3105
Main Authors: Kawahara, Sakie, Nakano, Ayako, Esumi, Tomoyuki, Iwabuchi, Yoshiharu, Hatakeyama, Susumi
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035102j