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Synlett 2000; 2000(2): 225-226
DOI: 10.1055/s-2000-6493
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Pseudomonas Cepacia Lipase Catalysed Synthesis of the Chiral Methacrylate Monomers by Kinetic Resolution of the Secondary Alcohols: Effect of the Substrate Structure on Enantioselectivity

Vilas Athawale* , Narendra Manjrekar
  • *Department of Chemistry, University of Mumbai, Vidyanagari, Mumbai-400 098, India; Fax +91 22 6 52 85 47; E-mail: polymerchemistry@yahoo.com
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Publication Date:
31 December 2000 (online)

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Optically active methacrylate monomers of secondary alcohols have been synthesised using oxime methacrylate as an acylating agent. The type of solvent used for the reaction had a profound effect on the reaction time and enantioselectivity. Various aryl, cyclic and linear secondary alcohols were screened for their structural effect on enantioselectivity. The nature and position of the substituents in the case of aryl carbinols, had a remarkable effect on the conversion and enantioselectivity, whereas, in the case of linear alcohols, the enantioselectivity was influenced by the increase in the chain length.

chiral methacrylate - enzymatic resolution - oxime methacrylate - secondary alcohols