Highly Enantioselective Aza Morita−Baylis−Hillman Reaction Catalyzed by Bifunctional β-Isocupreidine Derivatives
Journal of the American Chemical SocietyPublished 26 August 2008Open access
Nacim Abermil, Géraldine Masson, Jieping Zhu
Citations113
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TL;DR
The coexistence of two H-bond donors with different acidic strengths was found to be crucial for the observed high enantioselectivity of the aza-MBH reaction.
Abstract
The aza-MBH reaction of imines 1 and beta-naphthyl acrylate 2 in the presence of C-6' modified beta-isocupreidine derivative 1c (0.1 equiv) and beta-naphthol 5 (0.1 equiv) afforded the corresponding (3S)-aza-MBH adducts 4 in high yield and excellent enantiomeric excess. These catalytic conditions allowed the aliphatic imines to be employed for the first time as electrophilic partners of the aza-MBH reaction. The coexistence of two H-bond donors with different acidic strengths was found to be crucial for the observed high enantioselectivity.
Keywords
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