Decarbonylative Radical Coupling of α-Aminoacyl Tellurides: Single-Step Preparation of γ-Amino and α,β-Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A

A new radical-based coupling method has been developed for the single-step generation of various gamma-amino acids and alpha,beta-diamino acids from alpha-aminoacyl tellurides. Upon activation by Et3B and O-2 at ambient temperature, alpha-aminoacyl tellurides were readily converted into alpha-amino carbon radicals through facile decarbonylation, which then reacted intermolecularly with acrylates or glyoxylic oxime ethers. This mild and powerful method was effectively incorporated into expeditious synthetic routes to the pharmaceutical agent gabapentin and the natural product (-)-manzacidin A.