Baker's yeast reduction of α-(alkoxycarbonylamino)acetophenones and Lipase-catalysed resolution of 2-(alkoxycarbonylamino)-1-arylethanols

Enzymatic reduction of α-(alkoxycarbonylamino)acetophenones with baker's yeast afforded optically active (R)-2-(alkoxycarbonylamino)-1-arylethanols. However, the reduction of α-(benzyloxycarbonylamino)-4-methoxyacetophenone ( 3c ) with immobilized baker's yeast gave (S)-2-(benzyloxycarbonylamino)-1-(4-methoxyphenyl) ethanol. The lipase PS-catalysed transesterification of 2-(allyloxycarbonylamino)-1-arylethanols ( 5 ) using vinyl acetate as an acyl donor resulted in the formation of (S)-2-(allyloxycarbonyl-amino)-1-arylethyl acetates [( S )- 9 ] and (R)-2-(allyloxycarbonylamino)-1-aryle-thanols [( R )- 5 ].