ChemInform Abstract: 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.

Abstract

Decarbonylative Radical Coupling of -Aminoacyl Tellurides: Single-Step Preparation of -Amino and ,-Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A. --Aminoacyl tellurides (III) and (IX) generate -amino carbon radicals via decarbonylation. The radicals react with acrylates or glyoxylic oxime ethers yielding -amino esters or ,-diamino esters respectively. The stereoinformation of tellurides (IX) generated from (S)-amino acids is lost upon radical generation. The utility of this method is demonstrated in a short synthesis of gabapentin hydrochloride (XV). -(NAGATOMO, M.; NISHIYAMA, H.; FUJINO, H.; INOUE*, M.; Angew. Chem., Int. Ed. 54 (2015) 5, 1537-1541, http://dx.doi.org/10.1002/anie.201410186 ; Grad. Sch. Pharm. Sci., Univ. Tokyo, Bunkyo, Tokyo 113, Japan; Eng.) -Mais 24-223