Palladium-catalyzed oxamidation of alkenes: A new approach to benzoxazolidines

被引：15
|
作者：
Panda, Niranjan [1 ]
Yadav, Sushree Arpitabala [1 ]
机构：
[1] Natl Inst Technol, Dept Chem, Rourkela 769008, Odisha, India
来源：
TETRAHEDRON | 2018年 / 74卷 / 13期
关键词：
Oxamidation; Benzoxazolidine; Alkene; Sulfonamide; Protodepalladation; DOUBLE-MICHAEL REACTIONS; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; OXAZOLIDINE; OLEFINS; 1,3-OXAZOLIDINES; CYCLOADDITION; PYRROLIDINES; HETEROCYCLES;
D O I：
10.1016/j.tet.2018.02.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel palladium catalyzed protocol for the synthesis of benzoxazolidine by the reaction sulfamido-phenol and terminal alkene was developed. This oxamidation process is simple and does not require any ligand, base or inert atmosphere for the overall transformation. From control experiments, it is apparent that the cross-coupling reaction proceeds with initial formation of enesulfonamide which undergoes nucleopalladation by the intramolecular annulation and subsequent protodepalladation by TsOH to afford the benzoxazolidine. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1497 / 1504
页数：8
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