Intramolecular metal-catalyzed amination of pseudo-anomeric C-H bonds

被引：27
|
作者：
Toumieux, S [1 ]
Compain, P [1 ]
Martin, OR [1 ]
机构：
[1] Univ Orleans, CNRS, UMR 6005, Inst Chim Organ & Analyt, F-45067 Orleans, France
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 28期
关键词：
C-glycosides; Amination; C-H insertion; rhodium; N; O-acetals;
D O I：
10.1016/j.tetlet.2005.05.043
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular metal-catalyzed amination of a pseudo-anomeric C-H bond in a C-glycoside is reported. Treatment of a,alpha,beta-C-carbamoyloxymethyl- or beta-C-sulfamoyloxymethyl glycosides with Rh-2(OAc)(4), PhI(OAc)(2), and MgO provided original spiro-oxazolidines or spirooxathiazolidines in reasonable yields. No correlation between 'anomeric' stereochemistry and insertion efficiency was found for the conversion of carbamate derivatives whereas amination reactions of the corresponding sulfamate esters were found to be strongly dependent on the anomeric configuration. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4731 / 4735
页数：5
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