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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
Authors:Dr Masanori Nagatomo  Hayato Nishiyama  Haruka Fujino  Prof?Dr Masayuki Inoue
Institution:Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo‐ku, Tokyo 113‐0033 (Japan)
Abstract:A new radical‐based coupling method has been developed for the single‐step generation of various γ‐amino acids and α,β‐diamino acids from α‐aminoacyl tellurides. Upon activation by Et3B and O2 at ambient temperature, α‐aminoacyl tellurides were readily converted into α‐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.
Keywords:amino acids  natural products  radical reactions  tellurium  total synthesis
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