Asymmetric transfer of nitrenes catalyzed by chiral dirhodium(II) using aromatic sulfamate esters

被引：82

作者：

Fruit, C ^{[1
]}

Müller, P ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 06期

关键词：

D O I：

10.1016/j.tetasy.2004.01.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantioselective intra- and intermolecular insertions of aromatic sulfamate esters into activated C H bonds have been achieved via in situ generated phenyliodinanes in the presence of PhI(OAc)(2), MgO, and chiral Rh(II) catalysts. The optimal results were obtained with [Rh-2{(S)-nttl}(4)] and [Rh-2{(R)-ntv}(4)] as catalysts with up to 52% ee. In contrast, phenylsulfamates with allylic ortho-substituents reacted via intramolecular aziridination rather than insertion. The intermolecular amidation of indane proceeded with up to 97% yield when the reaction was carried out with the sulfamate in excess. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1019 / 1026

页数：8

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