Catalytic Asymmetric Passerini-Type Reaction: Chiral Aluminum−Organophosphate-Catalyzed Enantioselective α-Addition of Isocyanides to Aldehydes
2009-11-06T00:00:00Z (GMT) by
A chiral Lewis acid catalyst was prepared by mixing 2 equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et<sub>2</sub>AlCl. In the presence of a catalytic amount of [<b>4j</b>]<sub>2</sub>Al(III)Cl complex (0.05 equiv), reaction between α-isocyanoacetamides (<b>2</b>) and aldehydes (<b>3</b>) afforded the corresponding 5-aminooxazoles (<b>1</b>) in good yields and enantioselectivities. Complex [<b>4j</b>]<sub>2</sub>Al(III)Cl isolated as a white solid displayed similar reactivity as that prepared in situ.