A remarkable base-induced rearrangement of hydroxy oxazolines to amido tetrahydrofurans

KJ Wilson, M Sabat, GJ McGarvey

Index: Wilson, Kenneth J.; Sabat, Michal; McGarvey, Glenn J. Journal of Organic Chemistry, 1993 , vol. 58, # 23 p. 6180 - 6181

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Citation Number: 12

Abstract

Summary: Asymmetric 8-hydroxy oxazolines have been shown to rearrange at room temperature to isomeric tetrahydrofurans when deprotonated with potassium hydride in tetrahydrofuran. In the course of our investigations on the asymmetric elaboration of enantiomerically pure oxazoline 1, we observed varying amounts of undesirable contaminants accompanying some of these transformations.' Invariably, these contaminants appeared when the reaction proceeded ...