Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Alkynylations of Oxiranes with Lithium Acetylides by the Catalysis of Trimethylgallium
Yukitoshi FukudaSeijiro MatsubaraClaude LambertHiroshi ShiragamiToshiki NankoKiitiro UtimotoHitosi Nozaki
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1991 Volume 64 Issue 6 Pages 1810-1813

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Abstract

The reaction of 1-lithio-1-alkynes with oxiranes under the catalytic action of trimethylgallium afforded the corresponding β-hydroxy acetylenic compounds in good yields with excellent regioselectivities. No isomerization of oxiranes was observed during the reactions because of low Lewis acidity of trimethylgallium. The mechanism including activation of an oxirane by the coordination to trimethylgallium was proposed.

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