Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Organic and Biological
Syn-Effect” in the Conversion of (E)-α,β-Unsaturated Esters into the Corresponding β,γ-Unsaturated Esters and Aldehydes into Silyl Enol Ethers
Samar Kumar GuhaAtsushi ShibayamaDaisuke AbeMaki SakaguchiYutaka UkajiKatsuhiko Inomata
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2004 Volume 77 Issue 12 Pages 2147-2157

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Abstract

The stereochemistry in the conversion of (E)-α,β-unsaturated esters into the corresponding β,γ-unsaturated esters, and that in the conversion of aldehydes into the silyl enol ethers, were investigated. The Z/E ratios of the resulting β,γ-unsaturated esters and the silyl enol ethers varied according to the γ-substituents of the (E)-α,β-unsaturated esters and the α-substituents of the aldehydes, respectively. This phenomenon was rationalized by a “syn-effect”, which may be attributed primarily to a σ → π* interaction and/or 6π-electron homoaromaticity.

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© 2004 The Chemical Society of Japan
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