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

Nacim Abermil , Géraldine Masson (1, 2) , Jieping Zhu (3, 4, 5)

1 ICSN - Institut de Chimie des Substances Naturelles
2 INCM - Institut de neurosciences cognitives de la méditerranée - UMR 6193
3 UC Riverside - University of California [Riverside]
4 Department of Botany and Plant Sciences [Riverside]
5 State Key Lab of Estuarine and Coastal Research

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.

Domaines: Biologie cellulaire

Nacim Abermil, Géraldine Masson, Jieping Zhu. Highly enantioselective aza Morita-Baylis-Hillman reaction catalyzed by bifunctional beta-isocupreidine derivatives.. Journal of the American Chemical Society, 2008, 130 (38), pp.12596-7. ⟨10.1021/ja805122j⟩. ⟨hal-00337288⟩