Copper(I)-Catalyzed Asymmetric Addition of Terminal Alkynes to beta-Imino Esters: An Efficient and Direct Method in the Synthesis of Chiral beta(3)-Alkynyl beta(2,2)-Dimethyl Amino Acid Derivatives

Jun Wang, Zhihui Shao, Kai Ding, Wing Yiu Yu, Albert S. C. Chan

Research output: Contribution to journalArticlepeer-review

Abstract

The first catalytic asymmetric addition of terminal alkynes to β-imino esters was carried out using chiral copper(I) complexes as catalysts under mild reaction conditions, providing an efficient and direct synthetic approach to β3-alkynyl β2,2-dimethyl amino esters with yields of 73–97% and 48–90% ee. The rich chemistry of the alkynyl functionality makes the present method a powerful and versatile approach to a wide range of optically active β2,2-dimethyl amino acid derivatives.

Original languageEnglish
Pages (from-to)1250-1254
JournalAdvanced Synthesis & Catalysis
Volume351
Issue number9
DOIs
Publication statusPublished - 2009

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