Jump to main content
Jump to site search

Issue 66, 2020
Previous Article Next Article

Stereoselective amination via vinyl-silver intermediates derived from silver-catalyzed carboxylative cyclization of propargylamine

Author affiliations

Abstract

The stereoselective synthesis of aminovinyloxazolidinones based on the electrophilic amination of a vinyl-silver intermediate, generated by silver-catalyzed carbon dioxide incorporation on a propargyl amine, was achieved. The geometry of the aminated product was determined by a single crystal X-ray analysis and NOE measurement and it was elucidated that the geometry was proved to be opposite to the geometry predicted from the previous silver-catalyzed carbon dioxide fixation on a propargyl amine derivative. This unexpected stereoselectivity could be successfully explained by a radical mechanism.

Graphical abstract: Stereoselective amination via vinyl-silver intermediates derived from silver-catalyzed carboxylative cyclization of propargylamine

Back to tab navigation

Supplementary files

Article information


Submitted
28 Mar 2020
Accepted
07 Jul 2020
First published
20 Jul 2020

Chem. Commun., 2020,56, 9517-9520
Article type
Communication

Stereoselective amination via vinyl-silver intermediates derived from silver-catalyzed carboxylative cyclization of propargylamine

Y. Sadamitsu, K. Saito and T. Yamada, Chem. Commun., 2020, 56, 9517
DOI: 10.1039/D0CC02273J

Social activity

Search articles by author

Spotlight

Advertisements