Synthesis of Chiral α-Amino-diazoketones on Solid Support: An Access to β-Homologated Amino Acid Derivatives

Abstract Diazoketone derivatives were obtained on solid support from their corresponding α-amino acids anchored by their N-terminus to the resin. A complete study was performed to optimize the two steps process of this synthesis on solid support: activation of the carboxylic acid function followed b...

Full description

Saved in:
Bibliographic Details
Published in:Synlett 2004-12, Vol.2004 (15), p.2791-2793
Main Authors: Cantel, Sonia, Martinez, Jean, Fehrentz, Jean-Alain
Format: Article
Language:English
Subjects:
letter
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract Diazoketone derivatives were obtained on solid support from their corresponding α-amino acids anchored by their N-terminus to the resin. A complete study was performed to optimize the two steps process of this synthesis on solid support: activation of the carboxylic acid function followed by reaction with diazomethane. The obtained diazoketones were then submitted to Wolff rearrangement in the presence of an amine to yield the corresponding ­homologated amides or in the presence of water to yield the corresponding β-homologated amino acids.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-835639