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Catalysis of heterocyclic azadiene cycloaddition reactions by solvent hydrogen bonding: concise total synthesis of methoxatin

Academic Article
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Overview

related to degree

  • Glinkerman, Christopher, Ph.D. in Chemistry, Scripps Research 2013 - 2018

authors

  • Glinkerman, Christopher
  • Boger, Dale

publication date

  • September 2016

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Although it has been examined for decades, no general approach to catalysis of the inverse electron demand Diels-Alder reactions of heterocyclic azadienes has been introduced. Typically, additives such as Lewis acids lead to nonproductive consumption of the electron-rich dienophiles without productive activation of the electron-deficient heterocyclic azadienes. Herein, we report the first general method for catalysis of such cycloaddition reactions by using solvent hydrogen bonding of non-nucleophilic perfluoroalcohols, including hexafluoroisopropanol (HFIP) and trifluoroethanol (TFE), to activate the electron-deficient heterocyclic azadienes. Its use in promoting the cycloaddition of 1,2,3-triazine 4 with enamine 3 as the key step of a concise total synthesis of methoxatin is described.
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Identity

PubMed Central ID

  • PMC5042865

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/jacs.6b05438

PubMed ID

  • 27571404
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Additional Document Info

start page

  • 12408

end page

  • 12413

volume

  • 138

issue

  • 38

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