Download PDF
Synthesis 2007(2): 235-238  
DOI: 10.1055/s-2006-958950
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Methylenation and in situ Methanolation of Ketones Prone to C-C Double-Bond Isomerisation

Vidar Bjornstad, Kjell Undheim*
Department of Chemistry, University of Oslo, 0315 Oslo, Norway
Fax: +47(22)855507; e-Mail: kjell.undheim@kjemi.uio.no;
Further Information

Publication History

Received 11 October 2006
Publication Date:
21 December 2006 (online)

    Permissions and Reprints All articles of this category

Abstract

An efficient methylenation reaction in isomer-labile ketones is described. The methylenation reaction is based on an improved method for the formation of bis(iodozincio)methane [CH2(ZnI)2]. A subsequent in situ hydroboration-oxidation sequence provides the corresponding methanol derivatives in high yields without double-bond isomerisation.

Key words

enolisable ketones - methylenation - in situ alcohol formation - titanium-zinc promotion - CH2(ZnI)2 preparation