Novel lipase-catalysed enantioselective deacetylation of (+/-)-5-acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine.
(+/-)-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% ee.
Mukherjee
S
S
Department of Chemistry, University of Delhi, -110 007, Delhi, India.
Prasad
A K
AK
Parmar
V S
VS
Howarth
O W
OW
D000107:Acetylation; D000818:Animals; D002384:Catalysis; D007555:Isoxazoles / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D008968:Molecular Conformation; D013552:Swine
C435623:5-acetoxy-3-(4-fluorophenyl)-2-phenylisoxazolidine; D007555:Isoxazoles; D008049:Lipase