Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes.

Tao Yue , Mei-Xiang Wang , De-Xian Wang , Géraldine Masson (1) , Jieping Zhu (1)

1 ICSN - Institut de Chimie des Substances Naturelles

A chiral Lewis acid catalyst was prepared by mixing 2 equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et(2)AlCl. In the presence of a catalytic amount of [4j](2)Al(III)Cl complex (0.05 equiv), reaction between alpha-isocyanoacetamides (2) and aldehydes (3) afforded the corresponding 5-aminooxazoles (1) in good yields and enantioselectivities. Complex [4j](2)Al(III)Cl isolated as a white solid displayed similar reactivity as that prepared in situ.

Domaines: Biologie cellulaire

Tao Yue, Mei-Xiang Wang, De-Xian Wang, Géraldine Masson, Jieping Zhu. Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes.. Journal of Organic Chemistry, 2009, 74 (21), pp.8396-9. ⟨10.1021/jo9017765⟩. ⟨hal-00432449⟩