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The vinylogous intramolecular Morita-Baylis-Hillman reaction: synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts

Academic Article
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Overview

authors

  • Frank, S. A.
  • Mergott, D. J.
  • Roush, William

publication date

  • March 2002

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The development of the vinylogous intramolecular Morita-Baylis-Hillman reaction for the synthesis of functionalized cyclopentenes and cyclohexenes is described. The reaction involves the trialkyphosphine-catalyzed cyclization of 1,6- or 1,7-diactivated 1,5-hexadienes or 1,6-heptadienes, containing carboxyaldehyde, methyl ketone, or methoxycarbonyl as the olefin activating groups. A representative example of this reaction is the Me(3)P-catalyzed cyclization of 1a in tert-amyl alcohol, which provides the substituted cyclopentene 2a in 95% yield and with 97:3 regioselectivity.

subject areas

  • Alkylation
  • Catalysis
  • Cyclohexanes
  • Cyclohexenes
  • Cyclopentanes
  • Phosphines
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja017123j

PubMed ID

  • 11890766
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Additional Document Info

start page

  • 2404

end page

  • 2405

volume

  • 124

issue

  • 11

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