Synthesis 2004(9): 1307-1314  
DOI: 10.1055/s-2004-822363
PAPER
© Georg Thieme Verlag Stuttgart · New York

GaCl3-Catalyzed α-Ethenylation Reaction of Ketone

Ryo Amemiya, Yoshio Nishimura, Masahiko Yamaguchi*
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan
Fax: +81(22)2176811; e-Mail: yama@mail.pharm.tohoku.ac.jp;
Further Information

Publication History

Received 20 January 2004
Publication Date:
12 May 2004 (online)

Abstract

In the presence of catalytic amounts of GaCl3 (10 mol%) and 2,6-di(t-butyl)-4-methylpyridine (10 mol%), five- or six-membered ring ketones possessing α,α′-disubstituents are ethenylated at the α-carbon with triethylsilylethyne at 180 °C. The roles of the base are to inhibit decomposition of the products and to promote protodegallation of the organogallium intermediates.