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A “Traceless” Staudinger Ligation for the Chemoselective Synthesis of Amide Bonds

Organic Letters · 2000 · Vol. 2(14) · pp. 2141–2143
Eliana SaxonJoshua I. ArmstrongCarolyn R. Bertozzi

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.

Chemical Synthesis and AnalysisBiochemical and Structural CharacterizationClick Chemistry and ApplicationsChemistryAmideAzideStaudinger reactionCombinatorial chemistryPeptide bondPhosphineLigationStereochemistryOrganic chemistry

MeSH terms

AmidesChromatography, High Pressure LiquidIndicators and ReagentsMolecular Conformation

Funding

  • Division of Chemistry
Citations
652
FWCI
4.03
field-weighted impact
References
18
Percentile
94%
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Citations per year
Cited by
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Angewandte Chemie International Edition · 2009 · 3,061 citations
Organic Azides: An Exploding Diversity of a Unique Class of Compounds
Angewandte Chemie International Edition · 2005 · 2,175 citations
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A “Traceless” Staudinger Ligation for the Chemoselective Synthesis of Amide Bonds · Scinovex