Chemistry: A European Journal 2009-11-02

Copper-catalyzed amine-alkyne-alkyne addition reaction: an efficient method for the synthesis of gamma,delta-alkynyl-beta-amino acid derivatives.

Lei Zhou, Qi Shuai, Huan-feng Jiang, Chao-Jun Li

Index: Chemistry 15(43) , 11668-74, (2009)

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Abstract

A simple and efficient method for the synthesis of gamma,delta-alkynyl-beta-amino acid derivatives by a copper-catalyzed three-component amine-alkyne-alkyne addition reaction was developed. Various gamma,delta-alkynyl-beta-amino acid derivatives were synthesized in moderate to good yields in one step. With chiral prolinol derivatives employed as the amine component, excellent diastereoselectivities (up to >99:1 diastereomeric ratio (dr)) were obtained. The scope of the reaction and further transformations of the resulting amino acid derivatives, such as deprotection and cyclization are also described.