The Journal of organic chemistry

Reactions between Weinreb amides and 2-magnesiated oxazoles: a simple and efficient preparation of 2-acyl oxazoles

DJ Pippel, CM Mapes, NS Mani

Index: Pippel, Daniel J.; Mapes, Christopher M.; Mani, Neelakandha S. Journal of Organic Chemistry, 2007 , vol. 72, # 15 p. 5828 - 5831

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Citation Number: 35

Abstract

Despite the progress, the state-of-the-art for acyl oxazole synthesis remains less than ideal. Charged with providing multigram quantities of a potential new drug candidate bearing this structural motif, we became interested in developing a new approach to 2-acyl oxazoles. Because of the reported instability of 2-lithio oxazoles in THF at temperatures above −40 °C, 10 our first priority was to determine an alternative metal counterion. On the basis of recently reported ...