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

Vidar Bjornstad; Kjell Undheim

doi:10.1055/s-2006-958950

PAPER

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;

Abstract

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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

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References

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