Stereoselective synthesis of unsaturated and functionalized l-NHBoc amino acids, using Wittig reaction under mild phase-transfer conditions

…, J Bayardon, MJ Ondel-Eymin, S Jugé

Index: Remond, Emmanuelle; Bayardon, Jerome; Ondel-Eymin, Marie-Joelle; Juge, Sylvain Journal of Organic Chemistry, 2012 , vol. 77, # 17 p. 7579 - 7587

Full Text: HTML

Citation Number: 19

Abstract

The stereoselective synthesis of a new amino acid phosphonium salt was described by quaternization of melting triphenylphosphine with the γ-iodo NHBoc-amino ester, derived from l-aspartic acid. The deprotection of the carboxylic acid function to afford the phosphonium salt with a free carboxylic acid group was achieved by a palladium-catalyzed desallylation reaction. This phosphonium salt was used in the Wittig reaction with aromatic ...