Inverted regioselectivity of C-H amination: Unexpected oxidation at β- rather than γ-C-H

被引：12

作者：

Wyszynski, Filip J. ^{[1
]}

Thompson, Amber L. ^{[1
]}

Davis, Benjamin G. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 19期

基金：

英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;

关键词：

RH-CATALYZED AMINATION; INTRAMOLECULAR AMIDATION; ABSOLUTE-STRUCTURE; BONDS; FUNCTIONALIZATION; DERIVATIVES; CONVERSION; MECHANISM;

D O I：

10.1039/c0ob00113a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rare example of beta- over gamma-C-H selectivity during Rh-catalysed sulfamate ester cyclisation is presented; from derivatives of 1,6-anhydro-beta-D-mannopyranose, five-membered sulfamidates were formed in preference to the typical six-membered oxathiazinane intramolecular insertion products. A 3D structure of sulfamate 1 helps to rationalise this unusual selectivity and analyses suggest that n ->sigma*(CH) interactions may be a key controlling factor.

引用

页码：4246 / 4248

页数：3

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