Parallel kinetic resolution of active esters using designer oxazolidin-2-ones derived from phenylglycine

S Chavda, E Coulbeck, M Dingjan, J Eames…

Index: Chavda, Sameer; Coulbeck, Elliot; Dingjan, Marco; Eames, Jason; Flinn, Anthony; Northen, Julian Tetrahedron Asymmetry, 2008 , vol. 19, # 13 p. 1536 - 1548

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Citation Number: 13

Abstract

The parallel kinetic resolution of racemic pentafluorophenyl 2-phenylpropionate using an equimolar combination of quasi-enantiomeric oxazolidin-2-ones is discussed. The levels of diastereoselectivity were excellent (> 90% de) leading to separable quasi-enantiomeric oxazolidin-2-one adducts in good yield. This methodology was subsequently used to resolve a series of 2-aryl propionic and butanoic acids.