Concepedia

Synthesis of phosphonamidate peptides by Staudinger reactions of silylated phosphinic acids and esters

Ina Wilkening, Giuseppe Del Signore, Christian P. R. Hackenberger

Chemical Communications · 2010 · 73 citations · 29 references

DOI

Concepts

Abstract

The Staudinger reaction of unprotected azido-peptides with silylated phosphinic acids and esters on the solid support offers a straightforward acid-free entry to different phosphonamidate peptide esters or acids under mild conditions in high purity and yield.

References

29

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Stefan Bräse, Carmen Gil, Kerstin Knepper et al. · Angewandte Chemie International Edition · 2005 · 2.2K citations

, , +14

Lewis Base Catalysis in Organic Synthesis

Scott E. Denmark, Gregory L. Beutner · Angewandte Chemie International Edition · 2008 · 1.2K citations

, , +14

Recent advances in the staudinger reaction

Yuri G. Gololobov, L. F. Kasukhin · Tetrahedron · 1992 · 774 citations

, , +6

Design of Chiral <i>N</i>-Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and Its Application to Asymmetric Diels−Alder Reaction

Daisuke Nakashima, Hisashi Yamamoto · Journal of the American Chemical Society · 2006 · 501 citations

Asymmetric Brønsted Acid Catalysis: Enantioselective Nucleophilic Substitutions and 1,4‐Additions

Magnus Rueping, Boris J. Nachtsheim, Stefan A. Moreth et al. · Angewandte Chemie International Edition · 2007 · 347 citations

, , +14