161314-85-8Relevant articles and documents
Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional β-isocupreidine derivatives
Abermil, Nacim,Masson, Geraldine,Zhu, Jieping
supporting information; scheme or table, p. 12596 - 12597 (2009/04/10)
The aza-MBH reaction of imines 1 and β-naphthyl acrylate 2 in the presence of C-6′ modified β-isocupreidine derivative 1c (0.1 equiv) and β-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. Copyright