ABSOLUTE CONFIGURATION OF PINACOLYL ALCOHOL

The absolute configuration of (+)-pinacolyl alcohol (1), although widely assumed to be (5), has never been firmly established and there is reason to question the usual assignment. Direct chemical correlation with (+)-(S)-lactic acid firmly establishes that the absolute configuration usually assumed is indeed correct. The key step in the chemical correlation (Chart I) was the construction of the t-butyl group by hydrogenolysis of a 1-methyl-1-cyclopropane derivative (4). © 1969, American Chemical Society. All rights reserved.