Optically active fluorine-containing 3-hydroxybutyric acid ester

Details Optically active fluorine-containing 3-hydroxybutyric acid ester Optically active fluorine-containing 3-hydroxybutyric acid ester

1990-11-08

1992-06-02

Gray, Bruce

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

Organic compounds

Carboxylic acid esters

C07C 6466

Patent

active

051188368

ABSTRACT:
An optically active (3R)- or (3S)-fluorine-containing-3-hydroxybutyric acid ester represented by the formula: ##STR1## wherein R represents an alkyl group of C.sub.3 -C.sub.16 and A represents CF.sub.3, CHF.sub.2 or CH.sub.2 F, which is useful for synthesis of optically active substances, is prepared with high optical purity by ester exchange reaction between an alcohol represented by the formula:

REFERENCES:
Chemical abstracts 111:31747P (Jul. 24, 1989) No. 4 p. 621.
Chemical abstracts 112:6144C (Jan. 1, 1990) No. 1 p. 561.
Regeants for Organic Synthesis 8: 427 (1980).
Lin, et al., "A Microbially Based Approach for the Preparation of Chiral Molecules Possessing the Trifluoromethyl Group", J. Org. Chem. 1987, 52, 3211-3217.
Mori, et al., "Synthesis of Three Stereoisomeric Forms of 2-8, Dimethyl-1,7 Dioxaspiro[5.5] Undecane, the Main Component of the Cephalic Secretion of Andrena Wilkella", Tetrahedron vol. 37, No. 18, pp. 3221-3225, 1981.
Kitazume, et al., "Enzymatic Syntheses of Chiral Building Blocks With Trifluoromethyl Or Pentafluoroethyl Groups", Journal of Fluorine Chemistry, 29 (1985) 431-444.
New Syntheses of Physiologically Active Compounds Using the Chiral Synthons Produced by Microbial or Enzymatic Reactions--Journal of Synthetic Organic Chemistry, Japan 331 (Apr. 1987).

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