ChemInform Abstract: Reaction of (α,β-Epoxyalkyl)silanes with α-Sulfonyl Anions and α-Sulfonyl Anions in the Presence of a Lewis Acid. A Method for the Synthesis of (Z)-sec-Allylic Alcohols and β,γ -Unsaturated Alkyl Phenyl Sulfones.

Abstract

The reaction of 2-alkyl-3-(trimethylsilyl)oxiranes (1a or 1b) with anions generated from alkyl phenyl sulfones (2a-f) followed by hydrolysis affords sec-alkyl alcohols (3-7). An analogous reaction in the presence of BF 3 .Et 2 O affords adducts (8-11). Treatment of (8-11) with NaOH under phase-transfer conditions affords stereospecifically the corresponding allylic alcohols (4a-5c). Reaction of oxirane (1a) with anions derived from sterically hindered sulfones (2e) or (2f) in the presence of BF 3 .Et 2 O was investigated. Reaction of compounds (8), (9) with phosphorus tribromide in pyridine affords β,γ-unsaturated sulfones (19)