Free-Radical Version of the Strecker Synthesis of α-Aminoamides Promoted by Aqueous H2O2/TiCl3/HCONH2 System

Free-Radical Version of the Strecker Synthesis of α-Aminoamides Promoted by Aqueous H2O2/TiCl3/HCONH2 System

A new reaction of general synthetic interest representing the free-radical version of the Strecker synthesis to α-aminoamides is reported. A hydroxy radical, generated by Ti(III) one-electron reduction of H2O2, abstracts a H atom from the C−H bond of formamide, and the resulting carbamoyl radical ad...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 128; no. 16; pp. 5358 - 5359
Main Authors: Cannella, Rosalba, Clerici, Angelo, Panzeri, Walter, Pastori, Nadia, Punta, Carlo, Porta, Ombretta
Format: Journal Article
Language:English
Published: United States American Chemical Society 26-04-2006
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new reaction of general synthetic interest representing the free-radical version of the Strecker synthesis to α-aminoamides is reported. A hydroxy radical, generated by Ti(III) one-electron reduction of H2O2, abstracts a H atom from the C−H bond of formamide, and the resulting carbamoyl radical adds to the C atom of aldimines formed in situ, leading to a one-pot synthesis of α-aminoamides. Several types of aldehydes can participate in this process.
Bibliography:istex:1AEB50227D91F2133E7BEBDA3B13600AAEBE667A
ark:/67375/TPS-7JQ4VLJQ-J
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja061092g