Unusual reactions of diazocarbonyl compounds with α, β-unsaturated δ-amino esters: Rh(II)-catalyzed Wolff rearrangement and oxidative cleavage of N-H-insertion products

被引:2
|
作者
Nikolaev, Valerij A. [1 ]
Medvedev, Jury J. [1 ]
Galkina, Olesia S. [1 ]
Azarova, Ksenia V. [1 ]
Schneider, Christoph [2 ]
机构
[1] St Petersburg State Univ, Univ Prosp 26, St Petersburg 198504, Russia
[2] Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, Germany
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷
基金
俄罗斯基础研究基金会;
关键词
diazo compounds; N-H-insertion; oxidation cleavage; transition-metal-catalyzed reactions; Wolff rearrangement; DIAZO-COMPOUNDS; DIASTEREOSELECTIVE SYNTHESIS; CATALYZED DECOMPOSITION; AMMONIUM YLIDES; CAPROLACTAMATE; PYRROLIDINES; HETEROCYCLES; INDOLINES; KETONES; DOMINO;
D O I
10.3762/bjoc.12.180
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rh(II)-catalyzed reactions of aroyldiazomethanes, diazoketoesters and diazodiketones with alpha, beta-unsaturated delta-aminoesters, in contrast to reactions of diazomalonates and other diazoesters, give rise to the Wolff rearrangement and/or oxidative cleavage of the initially formed N-H-insertion products. These oxidation processes are mediated by Rh( II) catalysts possessing perfluorinated ligands. The formation of pyrrolidine structures, characteristic for catalytic reactions of diazoesters, was not observed in these processes at all.
引用
收藏
页码:1904 / 1910
页数:7
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