Dual Behavior of Isatin-Based Cyclic Ketimines with Dicarbomethoxy Carbene: Expedient Synthesis of Highly Functionalized Spirooxindolyl Oxazolidines and Pyrrolines

被引：54

作者：

Rajasekaran, T. ^{[1
]}

Karthik, G. ^{[1
]}

Sridhar, B. ^{[2
]}

Reddy, B. V. Subba ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

[2] CSIR Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 07期

关键词：

CARBONYL YLIDES; MULTICOMPONENT REACTIONS; STEREOSELECTIVE-SYNTHESIS; CATALYZED DECOMPOSITION; 3-COMPONENT REACTION; CYCLOADDITION; DIOXOLANES; ALDEHYDES; POTENT; AZIRIDINES;

D O I：

10.1021/ol400287q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereo-, regio-, and chemoselective method has been devised for the synthesis of a wide range of spirooxindolyl oxazolidines via an intermolecular 1,3-dipolar cycloaddition of carbonyl ylides generated from dimethyl diazomalonate and aromatic aldehydes, with cyclic ketimines using 5 mol % of Rh-2(OAc)(4) under mild conditions. Similarly, highly functionalized spirooxindolyl pyrrolines have also been prepared through 1,3-dipolar cycloaddition of azomethine ylides generated from dimethyl diazomalonate and cyclic ketimines, with dimethyl acetylenedicarboxylate.

引用

页码：1512 / 1515

页数：4