Process for the preparation of optically active hydroxyalkylphenols via asymmetric transfer hydrogenation of aryl ketones using chiral metal catalysts.

Abstract

Title compds. (I; n = 1-5; R1 = alkyl, alkenyl, alkynyl, organohalide, aryl, amino, amido) were prepd. via asym. transfer hydrogenation of aryl ketones (II; variables as above) using chiral metal catalysts. Thus, 1-(3-hydroxyphenyl)ethanone, (1R,2R)-chloro-N-(4-toluenesulfonyl-1,2-diphenylethylenediamine)(p-cymene)ruthenium, Et3N, and HCO2H were heated together to give 90% (R)-3-(1-hydroxyethyl)phenol in 99.3% enantiomeric excess. [on SciFinder(R)]