Tetrahedron: Asymmetry

Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles

A Kamal, GBR Khanna, R Ramu

Index: Kamal, Ahmed; Khanna; Ramu Tetrahedron Asymmetry, 2002 , vol. 13, # 18 p. 2039 - 2051

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Citation Number: 102

Abstract

A facile preparation of (±)-3-hydroxy-3-phenylpropanenitrile has been carried out by ring- opening of styrene oxide with NaCN in aqueous ethanol. Subsequent kinetic resolution of this material via lipase-mediated transesterification gave the S-alcohol and R-acetate in excellent yields and high enantioselectivities, particularly with lipase PS-C 'Amano'II. The effect of solvents and immobilization of the lipase has also been investigated. It is ...