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 Et sub(3)B and O sub(2) at ambient temperature, alpha -aminoacyl tellurides were readily converted...

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Published in:Angewandte Chemie 2015-01, Vol.127 (5), p.1557-1561
Main Authors: Nagatomo, Masanori, Nishiyama, Hayato, Fujino, Haruka, Inoue, Masayuki
Format: Article
Language:English
Subjects:
Activation
Ambient temperature
Carbon
Ethers
Joining
Oximes
Radicals
Tellurides
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container_issue 5
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container_title Angewandte Chemie
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creator Nagatomo, Masanori
Nishiyama, Hayato
Fujino, Haruka
Inoue, Masayuki
description 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 Et sub(3)B and O sub(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 (-)-manzacidinA.Original Abstract: Durch Aktivierung mit Et sub(3)B und O sub(2) bei Raumtemperatur werden [alpha]-Aminoacyltelluride durch Decarbonylierung in [alpha]-Aminokohlenstoffradikale ueberfuehrt, die in einer intermolekularen Reaktion mit Acrylaten oder Glyoxyloximethern [gamma]-Amino- und [alpha],[beta]-Diaminosaeuren bilden. Diese milde Methode wurde zur Synthese von Gabapentin und dem Naturstoff (-)-ManzacidinA verwendet.
doi_str_mv 10.1002/ange.201410186
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subjects Activation
Ambient temperature
Carbon
Ethers
Joining
Oximes
Radicals
Tellurides
title 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
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