Intramolecular Homolytic Substitution of Sulfinates and Sulfinamides

被引：43

作者：

Coulomb, Julien ^{[1
]}

Certal, Victor ^{[1
]}

Larraufie, Marie-Helene ^{[1
]}

Ollivier, Cyril ^{[1
]}

Corbet, Jean-Pierre ^{[2
]}

Mignani, Gerard ^{[2
]}

Fensterbank, Louis ^{[1
]}

Lacote, Emmanuel ^{[1
]}

Malacria, Max ^{[1
]}

机构：

[1] Univ Paris 06, UPMC, CNRS, Inst Parisien Chim Mol,UMR 7201, F-75005 Paris, France

[2] Ctr Rech Lyon, F-69192 St Fons, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 39期

关键词：

homolytic substitution; radical reactions; sulfinamides; sulfinates; sulfur heterocycles; RADICAL-CHAIN-REACTIONS; ACYL RADICALS; SULFUR ATOM; STEREOSELECTIVE-SYNTHESIS; CENTERED RADICALS; CARBON RADICALS; TANDEM REACTION; S(H)I REACTION; PHOSPHORUS; DERIVATIVES;

D O I：

10.1002/chem.200900942

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and efficient method for the synthesis of cyclic sulfinates and sulfinamides based on intramolecular homolytic substitution (S(H)1) at the sulfur atom by aryl or alkyl radicals is described. Both alkyl and benzofused compounds call be accessed directly from easily prepared acyclic precursors. Enantiomerically enriched sulfur-based heterocycles were formed through an S(H)i process with inversion of configuration at the sulfur atom cyclization of prochiral radicals proceeded with varying stereochemical outcomes, depending on the sire of the incoming radical 2-Pyridyl and 2-quinolyl radicals led to biaryl compounds, which result from attack onto the ortho position of the arylsulfinate rather than a thiophilic substitution.

引用

页码：10225 / 10232

页数：8

共 88 条

[1] Intramolecular homolytic substitution at selenium:: Synthesis of novel selenium-containing vitamin E analogues [J].