Asymmetric syntheses. Part V. The absolute configuration of some acetylenic alcohols
Abstract
(–)-But-3-yn-2-ol, (–)-hex-1-yn-3-ol, (–)-4-methylpent-1-yn-3-ol and (–)-oct-3-yn-2-ol have been prepared in 4—7% optical yield by reduction of the corresponding acetylenic ketones with 3-O-benzyl-1,2-O-cyclohexylidene-α-D-glucofuranose–lithium aluminium hydride complex. These alcohols have been assigned the S-configuration. The results underline the potential of the method for the preparation of asymmetric secondary carbinols.