Chiral polymers for the production of excess enantiomers

Details Chiral polymers for the production of excess enantiomers Chiral polymers for the production of excess enantiomers

1992-11-16

1994-01-25

Schofer, Joseph L.

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

Organic compounds

Carboxylic acids and salts thereof

562445, 562554, 562575, 562553, 564302, 564303, 564304, 526263, 526304, 526305, 526306, 5253267, 5253283, 5253595, 5253596, 525374, 525375, 525379, C07B 5700, C07B 5500, C07B 5300, C07C22730

Patent

active

052817504

ABSTRACT:
The present invention relates to chiral supports and to their use in the asymmetric synthesis, deracemization and optical inversion of organic chiral compounds. In particular, the supports are used in combination with thermal equilibration of a species having a reactive achiral portion. Preferably, these supports are obtained by the copolymerization of at least one chiral unit and at least one functionalizing unit or by the polymerization of at least one chiral unit which is a source of said functionalizing unit. Optionally, a crosslinking agent is utilized. By utilizing these supports and thermal equilibration, excess enantiomers can be produced.

REFERENCES:
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M. Calmes et al., "Polyacrylic Crosslinked Resins With Pendant Chirality As Auxiliary In Supported Asymmetric Synthesis," Tetrahedron Letters, Pergamon Journal, 27(36):4303-4306 (1986).
McArthur et al., "Polymer Supported Enantioselective Reactions.III.Protonation of Lithioenamine Derivatives of Racemic 2-Methylcyclohexanone," Can. J. Chem. 60:2984-45 (1982).
Frechet et al., "Polymer Assisted Asymmetric Reactions.II.*Synthesis and Application of a Crosslinked Resin Containing (R)14 1-(4-Vinylphenyl)Ethylamine," Reactive Polymers, 227-235 (1982).
Peter Marfey, "Determination of d-Amino Acids.II.Use of a Bifunctional Reagent, 1,5-Difluoro-2,4-Dinitrobenzene", Carlsberg Res. Commun., 49:591-596 (1984).
Colwell et al., "Synthesis of Carboxylic Acids and Esters Using Polymer-Bound Oxazolines," J. Org. Chem., 46:3097-3102 (1981).
Kawana et al., "Asymmetric Synthesis with Sugar Derivatives. V..sup.1,2) The Synthesis of .alpha.-Hydroxy Acids on Insoluble Polymer Supports," Bull. Chem. Soc. Japan, 47:160-165 (1974).
McArthur et al., "Polymer Supported Enantioselective Reactions.II. .alpha.-Methylation of Cyclohexanone", Can. J. Chem., 60:1836-1841 (1982).

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