Silver-Promoted Direct Phosphorylation of Bulky C(sp<sup>2</sup>)–H Bond to Build Fully Substituted β-Phosphonodehydroamino Acids
Hao‐Qiang Cao, Hao-Nan Liu, Zheyuan Liu, Baokun Qiao, Fa‐Guang Zhang, Jun‐An Ma
Abstract
A general and practical cross-dehydrogenative coupling protocol between readily available trisubstituted α,β-dehydro α-amino carboxylic esters and H-phosphites is described. This C(sp2)–H phosphorylation reaction proceeds with absolute Z-selectivity promoted by silver salt in a radical relay manner. The bulky tetrasubstituted β-phosphonodehydroamino acids were obtained in grams and added new modules to the toolkit for peptide modifications.
Topics & Concepts
ChemistryPhosphorylationMedicinal chemistryStereochemistryBiochemistryOrganophosphorus compounds synthesisCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions