Stereo-selective synthesis of 2-aryl-propionic acids of high opt

Details Stereo-selective synthesis of 2-aryl-propionic acids of high opt Stereo-selective synthesis of 2-aryl-propionic acids of high opt

1991-12-27

1993-09-28

Killos, Paul J.

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

Organic compounds

Carboxylic acids and salts thereof

562466, 562469, 562492, 562490, C07C 6206, C07C 53134

Patent

active

052488152

ABSTRACT:
The present invention relates to a stereospecific chemical synthesis of optically pure enantiomers of 2-aryl-alkanoic acids, especially those of the biologically active (S)-aryl-propionic acids, in good chemical yields, useful for preparing large quantities thereof, and having a high optical purity.

REFERENCES:
patent: 4209638 (1980-06-01), Nicholson et al.
Meyers, et al., Oxazolines. XIV. An Asymmetric Synthesis of R and S Dialkylacetic Acids from a Single Chiral Oxazoline, JACS, 96:20, Oct. 2, 1974, pp. 6508-6510.
Hoobler, et al., Origins of Steroselectivity in Asymmetric Syntheses Using Chiral Oxazolines, JACS, 100:26, Dec. 20, 1978, pp. 8182-8185.
Teulon, et al., Antiinflammatory and Analgesic Diastereoisomeric Derivatives of Indan-5-acetic Acid, Journal of Medicinal Chemistry, 1978, vol. 21, No. 9, pp. 901-905.
Yamaguchi, et al., Asymmetric Reductions with Chiral Reagents from Lithium Aluminum Hydride and (+)-(2S,3R)-4-Dimethylamino-3-methyl-1,2-diphenyl-2-butanol, J. Org. Chem., vol. 38, No. 10, (1973), pp. 1870-1877.
Yamaguchi, et al., A Reversal in Stereoselectivity Depending upon the Age of a Chiral Lithium Alkoxyaluminohydride Reducing Agent, JACS, 94:26, Dec. 27, 1972, pp. 9254-9255.
Hayashi, et al., Chiral (Beta-Aminoalkyl)phosphines, Highly efficient Phosphine Ligands for Catalytic Asmmetric Grignard Cross-Coupling, J. Org. Chem. 1983, 48, pp. 2195-2202.
Meyers, et al., The Synthetic Utility of 2-Oxazolines, Agnew. Chem. Int. Ed. Engl., vol. 15, (1976) No. 5, pp. 270-280.
Meyers, et al., Synthesis via 2-Oxazolines. IV. An Asymmetric Synthesis of 2-Methylalkanoic Acids from a Chiral Oxazoline, JACS, 95:1, Jan. 9, 1974, pp. 268-270.
Meyers, et al., Asymmetric Synthesis of R and S alpha-Alkylalkanoic Acids from Metalation and Alkylation of Chiral 2-Oxazolines, JACS, 98:2, Jan. 21, 1976, pp. 567-576.
Meyers, et al., Oxazolines. IX. Synthesis of Homologated Acetic Acids & Esters, J. Org. Chem., vol. 39, No. 18, 1974, pp. 2778-2783.
Kobler, et al., Synthese von Nitrilen mit Tetraalklammoniumcyaniden, Liebigs Ann. Chem., 1978, 1946-1962.

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