Stereospecific Desulfinylation of α,β-Epoxy Sulfoxides with Butyllithium. A New Synthesis of Epoxides and Allylic Alcohols from Carbonyl Compounds
- 1 August 1986
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 59 (8) , 2463-2470
- https://doi.org/10.1246/bcsj.59.2463
Abstract
Desulfinylation of α,β-epoxy sulfoxides, easily prepared from carbonyl compounds and 1-chloroalkyl phenyl sulfoxide, with 1 equivalent of butyllithium at low temperature gave epoxides in good yields. The similar α,β-epoxy sulfoxides having an arylmethyl group at the α-position gave 3-aryl-allylic alcohols upon treatment with excess butyllithium at −70 °C. These reactions offer a simple and useful approach to the synthesis of epoxides and 3-aryl-allylic alcohols from a carbonyl compound.Keywords
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