Synthesis of Oxindole-Appended Allyl Amines and Vinyl Aziridines via InCl3/ArSH-Mediated Ring Opening of Vinyl Aziridines and Sulfur Ylide Aziridination

被引：2

作者：

Lingam, Kandapalam Arun Prasath ^{[1
]}

Shanmugam, Ponnusamy ^{[1
]}

Mandal, Asit Baran ^{[2
]}

机构：

[1] Cent Leather Res Inst, Div Organ Chem, Council Sci & Ind Res, Chennai 600020, Tamil Nadu, India

[2] Cent Leather Res Inst, Chem Lab, Council Sci & Ind Res, Chennai 600020, Tamil Nadu, India

来源：

SYNLETT | 2012年 / 20期

关键词：

heterocycles; oxindole; ring opening; ylides; cyclization; CATALYTIC ASYMMETRIC AZIRIDINATION; COREY-CHAYKOVSKY REACTION; STEREOSELECTIVE-SYNTHESIS; CHIRAL AZIRIDINES; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; CYCLOPROPANATION; IMINES; REARRANGEMENT; ROUTE;

D O I：

10.1055/s-0032-1317556

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and efficient synthesis of oxindole-appended allyl amines and 3-vinylaziridine-2-oxindoles have been accomplished in good yield via InCl3/ArSH-mediated ring opening of 3-vinylaziridine-2-oxindoles and sulfur ylide aziridination, respectively. The sulfur ylide was generated in situ from the bromo isomerized Morita-Baylis-Hillman adduct of isatin with N-tosyl imines and tetrahydrothiophene under basic conditions.

引用

页码：2903 / 2908

页数：6

共 2 条

[1] Stereoselective Synthesis of Geometrically Strained, Oxindole-Appended Vinyl Cyclopropanes and Highly Substituted Cyclopentenes via Sulfur Ylide Cyclopropanation and Vinyl Cyclopropane Rearrangement
Lingam, Kandapalam Arun Prasath
Shanmugam, Ponnusamy
Selvakumar, Kodirajan
SYNLETT, 2012, (02) : 278 - 284
[2] TRIMETHYLSILYL IODIDE MEDIATED RING-OPENING OF VINYLCYCLOPROPANES AND VINYL-AZIRIDINES AS A MEANS OF (2+3) ANNULATIONS
HUDLICKY, T
FLEMING, A
SINAIZINGDE, G
SEOANE, G
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 193 : 29 - ORGN

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