Journal
TETRAHEDRON
Volume 62, Issue 1, Pages 236-242Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.09.114
Keywords
amino acids; Petasis reaction; multi-component coupling; boronic acid Mannich reaction
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The use of chiral secondary amines containing only one branched substituent has been shown to give optimal yields and stereoselectivities in the preparation of alpha-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. (c) 2005 Elsevier Ltd. All rights reserved.
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