ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE CYCLOHEXENOL DERIVATIVES VIA HIGHLY STEREOSELECTIVE REDUCTION OF (<i>R</i>)-3-(<i>p</i>-<i>t</i>-BUTYLPHENYLTHIO) CYCLOHEXAN-1-ONE

Abstract

Abstract (R)-3-(p-t-Butylphenylthio)cyclohexan-1-one was reduced with LiAlH(OBut)3 to afford (1S,3R)-3-(p-t-butylphenylthio)cyclohexan-1-o1, while the same reduction with LiBH(s-Bu)3 afforded the (1R,3R) counterpart almost exclusively. Elaboration of each product furnished both enantiomers of optically pure cyclohexenol derivatives.