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 ...

Related Articles:

Reactivity of chiral α-amidoalkylphenyl sulfones with stabilized carbanions. Stereoselective synthesis of optically active 1-aminopyrrolizidine

[Journal of Organic Chemistry, , vol. 69, # 21 p. 7303 - 7308]

Structure–activity study of l-amino acid-based N-type calcium channel blockers

[Bioorganic and Medicinal Chemistry, , vol. 11, # 8 p. 1901 - 1913]

The synthesis of a chiral β-amino acid derivative by the Grignard reaction of an aspartic acid equivalent

[Liu, Feng; Yu, Wansheng; Ou, Wenhua; Xu, Xiaojiong; Ruan, Libo; Wang, Xiaoke; Li, Yiming; Peng, Xijiang; Tao, Xiaohu; Mao, Jun; Wan, Jiaomei; Pan, Xianhua Journal of Chemical Research, 2010 , # 9 p. 517 - 519]

Reactivity of chiral α-amidoalkylphenyl sulfones with stabilized carbanions. Stereoselective synthesis of optically active 1-aminopyrrolizidine

[Journal of Organic Chemistry, , vol. 69, # 21 p. 7303 - 7308]

More Articles...