Stereospecific Desulfinylation of α,β-Epoxy Sulfoxides with Butyllithium. A New Synthesis of Epoxides and Allylic Alcohols from Carbonyl Compounds
作者:Tsuyoshi Satoh、Youhei Kaneko、Koji Yamakawa
DOI:10.1246/bcsj.59.2463
日期:1986.8
easily prepared from carbonylcompounds 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
A novel synthesis of epoxides and allylic alcohols from carbonyl compounds through α, β-epoxy sulfoxides
作者:Tsuyoshi Satoh、Youhei Kaneko、Koji Yamakawa
DOI:10.1016/s0040-4039(00)84534-7
日期:——
Treatment of α,β-epoxy sulfoxides, easily prepared from carbonyl compounds with 1 equivalent of n-butyllithium at −100 °C gave the desulfinated epoxides in good yields. The similar α,β-epoxy sulfoxides having arylmethyl group at α-position, on treatment with excess n-butyllithium at −70 °C afforded 3-aryl allylicalcohols.