Asymmetric synthesis of the enantiomers of the diarylcarbinol (1R)- and (1S)-1-(1-hydroxyphenylmethyl)-2-hydroxybenzene

Abstract

(1S)-1-Phenethyl(phenyl chromium tricarbonyl) ether (–)-4 undergoes completely stereoselective ortho-deprotonation with the thus formed carbanion being converted by the complementary sequences, benzoylation/hydride reduction and formylation/PhMgBr addition, to generate after decomplexation and deprotection the homochiral diarylcarbinols (–)-(1R)- and (+)-(1S)-1-(1-hydroxyphenylmethyl)-2-hydroxybenzene 1, respectively.