Process for producing optically active .gamma.-butyrolactone der

Details Process for producing optically active .gamma.-butyrolactone der Process for producing optically active .gamma.-butyrolactone der

1991-08-29

1995-05-30

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30512

Patent

active

054203066

ABSTRACT:
A process for producing an optically active .gamma.-butyrolactone derivative represented by formula (II): ##STR1## wherein R.sup.1 represents an alkyl group having from 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group; and * indicates an asymmetric carbon atom, is disclosed, comprising enantioselectively hydrogenating a .gamma.-keto acid or an ester thereof represented by formula (I): ##STR2## wherein R.sup.1 and * are as defined above; and R.sup.2 represents a hydrogen atom or a lower alkyl group, in the presence of an optically active ruthenium-phosphine complex. The compounds (I) can be obtained at high optical purity through simple operations and a reduced number of steps.

REFERENCES:
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patent: 5349107 (1994-09-01), Watanabe et al.
J. of Amer. Chem. Soc., vol. 110, No. 2, 20 Jan. 1988, pp. 629-631, Colubus, Ohio, U.S.; M. Kitamura et al: "Homogenous Asymmetric Hydrogenation of Functionalized Ketones".
J. of Amer. Chem. Soc., vol. 109, No. 19, 16 Sep. 1987, pp. 5856-5858, Colubus, Ohio., U.S.; R. Noyori et al.: "Asymmetric Hydrogenation of Beta-Keto Carboxylic Esters. A Practical, Purely Chemical Access to Beta-Hydroxy Esters in High Enantiomeric Purity".
J. of the Chem. Society, Communications No. 2, 1988, pp. 87-88, London, GB; H. Kawano et al.: "Ruthenium (II)-BINAP+ Catalysed Stereoselective Homogeneous Hydrogenation of 1,3-Diketones".
J. of the Chem. Society, Communications No. 13, 1985, 1 Jul. 1985, pp. 922-924, London, GB; T. Ikariya et al.: "Synthesis of Novel Chiral Ruthenium Complexes of 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl and their Use as Asymmetric Catalysts".
Fieser and Fieser's: "Reagents for Organic Synthesis" vol. 14, 1989, pp. 38-44, John Wiley & Sons, Inc., New York U.S., p. 41, 3rd paragraph--p. 42, first paragraph.

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