Diastereoselective Addition of Allyltrimethylsilane to N-Glyoxyloyl-(2R)-bornane-10,2-sultam. A new synthesis of (S)-1,2-Pentanediol

Abstract

Addition of allyltrimethylsilane (3) to N-glyoxyloyl-(2R)-bomane:0,2-sultam (4) in the presence of Lewis acid afforded, in high diastereoselecti vity, adduct (2'S)-6 which, after recrystallization, was hydrogenated to give optically pure (S)-1,2-pentanediol (1).