A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds

E Saxon; J I Armstrong; C R Bertozzi

doi:10.1021/ol006054v

A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds

Org Lett. 2000 Jul 13;2(14):2141-3. doi: 10.1021/ol006054v.

Authors

E Saxon¹, J I Armstrong, C R Bertozzi

Affiliation

¹ Department of Chemistry, University of California, Berkeley, California 94720, USA.

PMID: 10891251
DOI: 10.1021/ol006054v

Abstract

[reaction: see text] Here we report a novel modification of our previously reported "Staudinger ligation" that generates an amide bond from an azide and a specifically functionalized phosphine. This method for the selective formation of an amide bond, which does not require the orthogonal protection of distal functional groups, should find general utility in synthetic and biological chemistry.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Amides / chemical synthesis*
Amides / chemistry
Chromatography, High Pressure Liquid
Indicators and Reagents
Molecular Conformation

Substances

Amides
Indicators and Reagents

Grants and funding

GM58867-01/GM/NIGMS NIH HHS/United States