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Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones
Journal article   Peer reviewed

Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones

Najla Al Shaye, Sameer Chavda, Elliot Coulbeck, Jason Eames and Yonas Yohannes
Tetrahedron: asymmetry, Vol.22(4), pp.439-463
24/02/2011
DOI: https://doi.org/10.1016/j.tetasy.2011.02.021

Abstract

Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry, Physical Physical Sciences Science & Technology
The parallel resolution of racemic pentafluorophenyl 2-aryl/phenylpropanoates and butanoates using an equimolar combination of quasi-enantiomeric Evans oxazolidin-2-ones is discussed. The levels of diastereoselectivity were excellent (>90% de) leading to separable quasi-enantiomeric oxazolidin-2-ones in good yield. This methodology was used to resolve a series of structurally related 2-aryl/phenylpropanoic and butanoic acids. (C) 2011 Elsevier Ltd. All rights reserved.

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