PAPER	Synthesis 2006: 666-674   DOI: 10.1055/s-2006-926299
© Georg Thieme Verlag Stuttgart · New York
An Efficient CuI-Promoted Synthesis of Tri- and Tetrasubstituted Alkenes Using Organozinc Species
Song Xue*, Lin He, Yong-Kang Liu, Kai-Zhen Han, Qing-Xiang Guo
Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)3606689; e-Mail: xuesong@ustc.edu.cn;
Received 27 July 2005

Abstract

An efficient method for the synthesis of multifunctionalized alkenes has been developed. In the presence of 5 mol% CuI as catalyst, organozinc species CF₃COOZnEt, CF₃COOZnMe and CF₃COOZnPh reacted with α,β-acetylenic ketones and aldehydes in one pot providing trisubstituted alkenes in high yields with stereoselectivity. The reaction with β-substituted-α,β-acetylenic ketones gave tetrasubstituted alkenes in good yields with Z-isomers as the major products.

Key words

organozinc species - α,β-acetylenic ketones - aldehydes - multifunctionalized alkenes - CuI