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Preparation of 2-, 3-, and 4-Methylcarboxylic Acids and the Corresponding Alcohols of High Enantiopurity by Lipase-Catalyzed Esterification

  • Per Berglund
  • Erik Hedenström
Part of the Methods in Biotechnology book series (MIBT, volume 15)

Abstract

Chiral methyl-branched carboxylic acids or the corresponding alcohols of high enantiomeric purity are valuable intermediates for the synthesis of many pharmaceuticals, pesticides, and natural substances such as phero-mones. Often, compounds of a very high enantiomeric excess (>99.5% ee) are needed. Various methyl-branched carboxylic acids have been synthesized by chemical methods such as diastereoselective alkylation of alkylamide enolates bearing a chiral auxiliary (1). However, a loss in enantiomeric excess of about 2% ee is often associated with the final hydrolytic removal of the chiral auxiliary to release the chiral alkylated acid. This has been noted, for instance, with the currently popular auxiliary pseudo-ephe-drine (2), and much work has been devoted to overcome this obstruction, albeit with limited success so far (3).

Keywords

Immobilize Enzyme Enantiomeric Excess Alkanoic Acid Chiral Auxiliary Aqueous Sodium Carbonate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Humana Press Inc. 2001

Authors and Affiliations

  • Per Berglund
    • 1
  • Erik Hedenström
    • 2
  1. 1.Department of BiotechnologyRoyal Institute of TechnologyStockholmSweden
  2. 2.Department of Chemistry and Process TechnologyMid Sweden UniversitySundsvallSweden

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