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

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

Rh(II)-сatalyzed reactions of aroyldiazomethanes, diazoketoesters and diazodiketones with α,β-unsaturated δ-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. Th...

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Bibliographic Details
Main Authors: Valerij A. Nikolaev, Jury J. Medvedev, Olesia S. Galkina, Ksenia V. Azarova, Christoph Schneider
Format: Article
Language:English
Published: Beilstein-Institut 2016-08-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
diazo compounds
N–H-insertion
oxidation cleavage
transition-metal-catalyzed reactions
Wolff rearrangement
Online Access:https://doi.org/10.3762/bjoc.12.180
Description
Summary:Rh(II)-сatalyzed reactions of aroyldiazomethanes, diazoketoesters and diazodiketones with α,β-unsaturated δ-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.
ISSN:1860-5397

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