A Synthetic Route to Chiral Dihydrobenzothiazines through Ring Opening of Activated Aziridines with 2-Halothiophenols/Copper-Powder-Mediated C-N Cyclization

被引：19

作者：

Ghorai, Manas K. ^{[1
]}

Sayyad, Masthanvali ^{[1
]}

Nanaji, Yerramsetti ^{[1
]}

Jana, Sourita ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2015年 / 10卷 / 07期

关键词：

copper; asymmetric synthesis; aziridines; regioselectivity; stereoselectivity; COPPER-CATALYZED AMINATION; ATP-CHANNEL OPENERS; ARYL HALIDES; COUPLING REACTION; 1,4-BENZOTHIAZINE DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; ROOM-TEMPERATURE; MESO-AZIRIDINES; BOND FORMATION; AMINO-ACIDS;

D O I：

10.1002/asia.201500153

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple protocol for the synthesis of dihydrobenzothiazines through regio- and stereoselective S(N)2-type ring opening of N-tosylaziridines with sulfur nucleophiles followed by copper-powder-mediated intramolecular C-N cyclization in excellent yields (up to 95%) with high diastereo- and enantioselectivity (up to >99%) is reported.

引用

页码：1480 / 1489

页数：10

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