Regioselective Substitutions of Unsymmetrical 1,2-Diols using Dioxaphospholanes: Applications to Carbohydrates

Abstract

For several years, the method employing 1,3,2λ⁵dioxaphospholanes to effect regioselective substitution of unsymmetrical 1,2-diols has been investigated.^[1] As carbohydrates are an abundant source of diols, this study has been extended to the use of 1,2-O-isopropylidene- D-ghCOfuranOSe 1. We have synthesized a single dioxaphospholane 2 and subsequently treated it with trimethylsilyltriflate to form oxyphosphonium ions 3 and 4.