Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines
Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines
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DOI：
10.1016/s0040-4020(98)00500-6
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发表时间：
1998-08-27
期刊：
影响因子：
2.1
通讯作者：
Zhou, P
中科院分区：
文献类型：
--
作者：
Davis, FA;Liu, H;Zhou, P
研究了1，3-二羰基化合物在环体系和非环体系中与邻苯二甲酰磺酰基氧氮杂环丙烷2的氧化反应。两个反应途径被确定：烯醇化α-羟基化和一个新的Baeyer-Villiger型氧化。Baeyer-Villiger氧化产物仅在酮中观察到，并通过烷氧基环氧化物的重排产生。仅在酮基为6元环的一部分的β-酮酯的烯醇化物中观察到合成有用的ee（82-95%）。(C)1998爱思唯尔科技有限公司版权所有。
The oxidation of 1,3-dicarbonyl compounds with (camphorylsulfonyl)oxaziridines 2 was studied in both cyclic and acyclic systems. Two reaction pathways were identified: enolate alpha-hydroxylation and a novel Baeyer-Villiger type oxidation. The Baeyer-Villiger oxidation product was observed only for the ketones and arises via rearrangement of an alkoxy epoxide. Synthetically useful ee's (82-95%) were observed only for enolates of beta-ketoesters where the keto group is part of a 6-membered ring. (C) 1998 Elsevier Science Ltd. All rights reserved.