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Novel lipase-catalysed enantioselective deacetylation of (+/-)-5-acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine

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UNSPECIFIED. (2001) Novel lipase-catalysed enantioselective deacetylation of (+/-)-5-acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 11 (16). pp. 2117-2121. ISSN 0960-894X

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Abstract

(+/-)-5-Acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine has been synthesised by a highly diastereoselective [3+2] cycloaddition reaction between alpha-(4-fluorophenyl)-N-phenylnitrone and vinyl acetate in good yield. Candida rugosa lipase catalyses the deacetylation of this (+/-)-5-acetoxyisoxazolidine in a highly enantioselective fashion in diisopropyl ether containing n-butanol affording (-)-5-acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine in 43% yield and > 99% cc. (C) 2001 Elsevier Science Ltd. All rights reserved.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Journal or Publication Title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
ISSN: 0960-894X
Date: 20 August 2001
Volume: 11
Number: 16
Number of Pages: 5
Page Range: pp. 2117-2121
Publication Status: Published
URI: http://wrap.warwick.ac.uk/id/eprint/11893

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