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Multicomponent One-Pot Procedure for the Synthesis of Free α-Chiral Amines from Aldehydes

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Alexandre Côté and André B. Charette*

Dpartement de Chimie, Universit de Montral, P.O. 6128, Station Downtown, Montral, Qubec, Canada H3C 3J7 andre.charette@umontreal.ca

J. Org. Chem., 2005, 70 (26), pp 10864–10867

DOI: 10.1021/jo0516483

Publication Date (Web): November 18, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

The synthesis of free α-chiral amines by a one-pot multicomponent procedure from commercially available starting materials is described. This enantioselective reaction involves a catalytic asymmetric addition of dialkylzinc reagents to N-diphenylphosphinoylimines with use of an air-stable precatalyst complex 1. The α-chiral amines are prepared with a one-pot procedure from alkyl and aryl aldehydes in good yield (41−90%) and with excellent enantioselectivity (90−97% ee).

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Published In Issue December 23, 2005
Received August 5, 2005

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Multicomponent One-Pot Procedure for the Synthesis of Free α-Chiral Amines from Aldehydes