Synthesis of 4-carboethoxy-4-oxazolin-2-ones from 3-nosyloxy-2-ketoesters

RV Hoffman, MC Johnson, JF Okonya

Index: Hoffman, Robert V.; Johnson, M. Catherine; Okonya, John F. Tetrahedron Letters, 1998 , vol. 39, # 11 p. 1283 - 1286

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Citation Number: 10

Abstract

We recently described the preparation of 3-nosyloxy-2-ketoesters 1 from a-ketoesters and some aspects of their use as precursors for the synthesis of 1,2,3_functionalized products.1 In contrast to the isomeric 2-nosyloxy-3-ketoesters 2 which are extraordinarily versatile intermediates,2 the synthetic utility of 1 is compromised by the extreme electrophilicity of the ketone carbonyl group which dominates the chemistry of 1. For example, the carbonyl group of 1 hydrates ...