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
收藏
页码：4246 / 4248
页数：3
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