The Stereospecific Tert-Butyllithium Reduction of Triene Sulfoxides: Improved Levels of Deuterium Incorporation

Abstract

Treatment of triene sulfoxides with t-BuLi and methanol-O-d₁ in D₂O-wet ether leads to trienes with practical levels (96%) of deuterium incorporation. Alternatively, successive treatment of triene sulfoxides dwith CH₃Li and then t-BuLi followed by methanol-O-d₁ quench affords similar levels of label incorporation.