Journal
ORGANIC LETTERS
Volume 5, Issue 17, Pages 3103-3105Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol035102j
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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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