β-Isocupreidine-Catalyzed Asymmetric Baylis−Hillman Reaction of Imines
Organic Letters2003Vol. 5(17), pp. 3103–3105
Citations Over TimeTop 1% of 2003 papers
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.
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