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Intramolecular Diels-Alder reactions of cyclopropenone ketals

Academic Article
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Overview

related to degree

  • Patel, Paresma, Ph.D. in Organic Chemistry, Scripps Research 2005 - 2010

authors

  • Patel, Paresma
  • Boger, Dale

publication date

  • August 2010

journal

  • Organic Letters  Journal

abstract

  • The first intramolecular cycloaddition reactions of cyclopropenone ketals with tethered electron-deficient, electron-rich, and neutral 1-substituted dienes are reported, constituting inverse electron demand, normal, and neutral Diels-Alder reactions, that provide exclusively the exo [4 + 2] cycloaddition products without the intervention of [1 + 2], [3 + 2], or [3 + 4] cycloadducts in reactions whose courses do not depend on the reaction conditions, the diene activating substituent, or the nature of the tethering.

subject areas

  • Cyclization
  • Cyclopropanes
  • Ethers, Cyclic
  • Molecular Structure
  • Polyenes
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC2912946

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol101375a

PubMed ID

  • 20614867
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Additional Document Info

start page

  • 3540

end page

  • 3543

volume

  • 12

issue

  • 15

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