Journal article

Factors affecting the efficiency and stereoselectivity of alpha-amino acid synthesis by the Petasis reaction

TJ Southwood, MC Curry, CA Hutton

TETRAHEDRON | PERGAMON-ELSEVIER SCIENCE LTD | Published : 2006

Abstract

The use of chiral secondary amines containing only one branched substituent has been shown to give optimal yields and stereoselectivities in the preparation of α-amino acids using the Petasis reaction. While the use of chiral primary amines generally gives products in low to moderate diastereoselectivity, chiral secondary amines generally give products in >95:5 diastereoselectivity. Additionally, the use of amines with two chiral (and by definition, branched) N-alkyl substituents results in significantly reduced yields with respect to to secondary amines with one or no branched N-alkyl substituents. © 2005 Elsevier Ltd. All rights reserved.

University of Melbourne Researchers