Novel, Light-Emitting Reaction of (E)-2-(Phenylsulfonyl)-3-phenyloxaziridine with Strong Bases

MN Stojanovic, Y Kishi

Index: Stojanovic, Milan N.; Kishi, Yoshito Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9921 - 9922

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Citation Number: 5

Abstract

Davis' oxaziridine (1) is widely used in organic synthesis. One of its important applications is the hydroxylation of enolates, yielding a-hydroxy ketones (Scheme l). 3 For example, addition of 1 in tetrahydrofuran to a solution of the enolate of 3 in THF under a nitrogen atmosphere yielded the expected a-hydroxy ketone 4 in 75% yield. However, when more than 2 equiv of lithium diisopropylamide (LDA) was used, 1 instantaneously decomposed ...