110902-38-0Relevant academic research and scientific papers
A Convenient Preparation of Optically Acitve 1,1'-Binaphthyl-2,2'-diol via Enzymatic Hydrolysis of the Racemic Diester
Miyano, Sotaro,Kawahara, Kan,Hashimoto Harukichi
, p. 355 - 356 (1987)
Commercially available porcine pancreatic lipase can conveniently be utilized for a highly enantioselective hydrolysis of valeric acid diester of racemic 1,1'-binaphthyl-2,2'-diol to gave the (S)-diol (95percent ee at 46 percent conversion).
Resolution of Binaphthols and Spirobiindanols Using Cholesterol Esterase
Kazlauskas, Romas J.
, p. 4953 - 4959 (2007/10/02)
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 -2,2'-diol (1) and 2,2',3,3'-tetrahydro-3,3,3',3'-tetramethyl-1,1'-spirobi-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.
