ScienceDirect - Tetrahedron Letters : Palladium-catalyzed construction of amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions

Tetrahedron Letters
Volume 46, Issue 39, 26 September 2005, Pages 6663-6666

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doi:10.1016/j.tetlet.2005.07.139

Palladium-catalyzed construction of amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions

Daiji Ikeda^a, Motoi Kawatsura^a^,^b^,^, and Junichi Uenishi^a

^aKyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan ^bFaculty of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan

Received 7 July 2005;

revised 28 July 2005;

accepted 28 July 2005.

Available online 15 August 2005.

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Abstract

The palladium catalyzed regio- and diastereo-selective allylic alkylation of (R)-2-acetoxy-4-aryl-3-butene with N-(diphenylmethylidene)glycinate and N-(diphenylmethylidene)alaninate occurred. The stereochemistry was controlled by the use of o-(diphenylphosphino)carboxylic acid, and produced new amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions.