Decarbonylative Radical Coupling of [alpha]-Aminoacyl Tellurides: Single-Step Preparation of [gamma]-Amino and [alpha],[beta]-Diamino Acids and Rapid Synthesis of Gabapentin and ManzacidinA

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 O2 at ambient temperature, [alpha]-aminoacyl tellurides were readily converted into [al...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2015-01, Vol.127 (5), p.1557
Main Authors: Nagatomo, Masanori, Nishiyama, Hayato, Fujino, Haruka, Inoue, Masayuki
Format: Article
Language:ger
Subjects:
Chemistry
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 O2 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 (-)-manzacidinA.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201410186