Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines

被引：54
|
作者：
Davis, FA [1 ]
Liu, H
Chen, BC
Zhou, P
机构：
[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
[2] Drexel Univ, Dept Chem, Philadelphia, PA 19104 USA
来源：
TETRAHEDRON | 1998年 / 54卷 / 35期
关键词：
D O I：
10.1016/S0040-4020(98)00500-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：10481 / 10492
页数：12
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