Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Zinc Metal-Promoted Stereoselective Olefination of Aldehydes and Ketones with gem-Dichloro Compounds in the Presence of Chlorotrimethylsilane
Yoshio IshinoMasatoshi MiharaShintaro NishihamaIkuzou Nishiguchi
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1998 Volume 71 Issue 11 Pages 2669-2672

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Abstract

A combination of zinc metal and a catalytic amount of chlorotrimethylsilane has been found to promote the transformation of various aldehydes and ketones with gem-dichloro compounds, such as benzylidene dichloride (1a) and methyl dichloroacetate (1b), to the corresponding cross-coupling products, such as substituted styrene 3 and methyl acrylates 4 derivatives, under mild reaction conditions in THF. The E-isomer of the corresponding alkenes was obtained stereoselectively in good-to-excellent yields. The reaction serves as a very convenient one-pot procedure.

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© 1998 The Chemical Society of Japan
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