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Remarkable phosphine-effect on the intramolecular aldol reactions of unsaturated 1,5-diketones: highly regioselective synthesis of cross-conjugated dienones

Academic Article
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Overview

authors

  • Thalji, R. K.
  • Roush, William

publication date

  • December 2005

journal

  • Journal of the American Chemical Society  Journal

abstract

  • We report a phosphine-mediated intramolecular aldol cyclization of unsaturated diketones that proceeds with extremely high levels of regioselectivity for the cross-conjugated bicyclic dienone products. The sense of regioselectivity observed in this reaction is complementary to that obtained using traditional aldol conditions. Experimental evidence that supports the involvement of a phosphine Michael adduct is described.

subject areas

  • Alkenes
  • Cyclization
  • Cycloparaffins
  • Ketones
  • Phosphines
  • Stereoisomerism
  • Vinyl Compounds
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Identity

PubMed Central ID

  • PMC2515627

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0540851

PubMed ID

  • 16316211
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Additional Document Info

start page

  • 16778

end page

  • 16779

volume

  • 127

issue

  • 48

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