Enantiomeric enrichment of bicyclic alcohols

Details Enantiomeric enrichment of bicyclic alcohols Enantiomeric enrichment of bicyclic alcohols

1995-08-15

1998-03-10

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 80, C07C 6934

Patent

active

057263442

ABSTRACT:
There is disclosed a two-stage enzymatically catalyzed reaction for the selective preparation of the (R)-endo-isomer of norbornenol from a mixture containing all four stereo- and regioisomers of norbornenol, as well as the synthesis of the intermediate product comprising the enantiomerically enriched mono-ester of (R)-endo-norbornenol and a diacid, and of the enantiomerically enriched saturated alcohol (R)-endo-norborneol. There is also disclosed a method for the production of (R)-endo-norborne-2-ol, by chemical reduction of either the enantiomerically enriched monoester and subsequent hydrolysis, or by hydrolysis of the enantiomerically enriched monoester and then chemical reduction.

REFERENCES:
patent: 4264754 (1981-04-01), Kageyama et al.
patent: 5270206 (1993-12-01), Saccomano
Irwin et al., "Alcohol Dehydrogenase Catalyzed Oxidoreductions," 98 J.A.C.S. 8476 (1976).
Kasper et al; CA 98:143807C, 1983.
Hueckel et al.; CA66:1966, 1967.
CA98:143807 (1982).
CA66:1966 (1966).

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