Resolution of Binaphthols and Spirobiindanols Using Cholesterol Esterase

Article abstract of DOI:10.1021/ja00195a059

Cholesterol esterase (EC 3.1.1.13) catalyzes the hydrolysis of steroid, binaphthol, and spirobiindanol esters.The hydrolysis of binaphthol and spirobiindanol esters is enantiospecific and can be used to resolve these materials.Simple, synthetic-scale (200 g) procedures are detailed for the resolution of <1,1'-binaphthalene>-2,2'-diol (1) and 2,2',3,3'-tetrahydro-3,3,3',3'-tetramethyl-1,1'-spirobi<1H-indene>-6,6'-diol (6).Resolution of 1 involved hydrolysis of the dipentanoate ester catalyzed by crude, inexpensive enzyme (bovine pancreas acetone powder) and yielded each enantiomer in > 60percent of theoretical yield with >/= 99percent enantiomeric purity.Similar resolution of 6 by hydrolysis of the dihexanoate ester yielded each enantiomer in > 50percent of theoretical yield with > 95percent enentiomeric purity.These resolution involve two enzymic reactions: hydrolysis of the diester to the monoester followed by hydrolysis of the monoester to the diol.A theoretical analysis of such two-step resolutions suggests that two-step resolutions can yield products with higher enantiomeric purity than can single-step resolutions.