Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional beta-isocupreidine derivatives

Journal of the American Chemical Society
Nacim AbermilJieping Zhu

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.

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Aug 10, 2010·Journal of the American Chemical Society·Takafumi YukawaMasakatsu Shibasaki
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