Process for producing optical active 4-hydroxy-2-cyclopentenone

Details Process for producing optical active 4-hydroxy-2-cyclopentenone Process for producing optical active 4-hydroxy-2-cyclopentenone

1993-03-12

1995-03-07

Reamer, James H.

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

Organic compounds

Oxygen containing

568379, C07C 4585

Patent

active

053959779

ABSTRACT:
A process for producing optically active 4-hydroxy-2-cyclopentenone [1] which comprises reacting 4-hydroxy-2-cyclopentenone represented by the formula: ##STR1## with an optically active propargyl alcohol derivative represented by the general formula: ##STR2## wherein R and R.sup.1 each independently represent a halogenated phenyl group, an alkylphenyl group, or an alkyl group which may be substituted with one or more halogen atom(s), and * indicates an asymmetric carbon atom, to form an optically active complex [3] consisting essentially of optically active 4-hydroxy-2-cyclopentenone represented by the formula [1] ##STR3## wherein * indicates an asymmetric carbon atom, and the optically active propargyl alcohol derivative [2], and then decomposing the optically active complex [3].

REFERENCES:
patent: 4683341 (1987-07-01), Ishii et al.
patent: 5041620 (1991-08-01), Toda et al.
Koichi Tanaka et al., "Efficient Optical Resolution of Some Key Compounds of Prostaaglandin Synthesis" Tetrahedron: Asymmetry, vol. 3, No. 4, 1992, Oxford, England, pp. 517-520.
Funio Toda et al., "Optical Resolution of Bicyclo (2.2.1) Heptanone, Bicyclo (2.2.2) Octanone, and Bicyclo (3.2.1) Octanone Derivatives by Inclusion Complexation with Optically Active Host Compounds", Journal of Organic Chemistry, vol. 56, 1991, Easton U.S., pp. 7332-7335.
Japanese publication No. 88-246713, Sumitomo Chemical Ind. K.K., Database WPI, Derwent Publications Ltd., London, England (abstract) (1988).
Summary of Lecture on "Asymmetric Recognition and Optical Resolution Utilizing Molecular Aggregtes" No. 63 1992, spring, fumio toda The Chemical Society of Japan.

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