Optically active cyclopentenols and process for preparing the sa

Details Optically active cyclopentenols and process for preparing the sa Optically active cyclopentenols and process for preparing the sa

1990-08-13

1992-04-21

Lone, Werren B.

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

Organic compounds

Oxygen containing

560231, 554229, C07C 3506, C07C 6902

Patent

active

051070391

ABSTRACT:
Optically active cyclopentenols are here disclosed which are represented by the formula (I) ##STR1## (wherein R is a hydrogen atom or an acyl group having 2 to 15 carbon atoms, and the sign * denotes a chiral carbon atom).
The optically active cyclopentenols can be prepared by a process which comprises the step of carrying out a transesterification between (.+-.)-cyclopentenol represented by the formula (IV) ##STR2## and triglyceride or vinyl ester by the use of esterase to obtain an optically active cyclopentenol represented by the formula (II) ##STR3## and an optically active cyclopentenol derivative represented by the formula (III) ##STR4## (wherein R' is an acyl group having 2 to 15 carbon atoms, and the sign * denotes a chiral carbon atom) which is a derivative of the enantiomer of the cyclopentenol (II); or alternatively, by another process which comprises the step of hydrolysis or alcoholysis of an optically active cyclopentenol derivative represented by the formula (III) ##STR5## (wherein R' is an acyl group having 2 to 15 carbon atoms, and the sign * denotes a chiral carbon atom) to obtain an optically active cyclopentenol represented by the formula (II) ##STR6## having the same absolute configuration as in the aforesaid derivative.

REFERENCES:
patent: 3344191 (1967-09-01), Chappell
Gasson et al., "J. Chem. Soc." pp. 2798-2800 (1950).
English et al., "J. Amer. Chem. Soc." vol. 74 pp. 1909-12 QDI.A5.
Wiemann et al., "Chemical Abstract" vol. 37, p. 1933 1957.
Brown et al., "Chem. & Eng. News" pp. 36-37 (Jan. 19, 1959).
Huckel et al., "Ann. der Chemie", vol. 649, pp. 13-20 (Nov. 1961).

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