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Type: Journal article
Title: Asymmetric induction in acyclic radical reactions: Enantioselective syntheses of a-Amino acids via carbon-carbon bond forming radical reactions
Author: Hamon, David P. G.
Massy-Westropp, Ralph A.
Razzino, Pasquale
Citation: Tetrahedron, 1995; 51(14):4183-4194
Publisher: Pergamon
Issue Date: 1995
ISSN: 0040-4020
School/Discipline: School of Chemistry and Physics : Chemistry
Statement of
David P.G. Hamon, Ralph A. Massy-Westropp and Pasquale Razzino
Abstract: The derivative of glycine, 8-phenylmenthyl N-Boc-2-bromoglycinate 1 reacted with allyltri-n-butylstannanes via the corresponding radical 2 by the SH2′ mechanism to give (2S) allyl amino acid drrivatives with high diastereoselectivity. The reaction of 1 with triphenyl(1,2-propadienyl)stannane and triphenyl(2-propynyl)stannane gave the (2S) allenyl and (2S) propargyl amino acid derivatives respectively also with high diastereoselectivity but by a different mechanism. The 2-bromoglycinate 1 reacted with various allyltri-n-butylstannanes, triphenyl(1,2-propadienyl)stannane and triphenyl(2-propynyl)stannane to give (2S) unsaturated amino acid derivatives with high diastereoselectivity.
Description: Available online 29 March 2000.
Rights: Copyright © 1995 Published by Elsevier Ltd.
DOI: 10.1016/0040-4020(95)00134-T
Appears in Collections:Chemistry publications

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