Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes

Roohollah Kazem Shiroodi, Alexander S. Dudnik, Vladimir Gevorgyan

Research output: Contribution to journalArticle

37 Scopus citations

Abstract

A double migratory cascade reaction of α-halogen-substituted propargylic phosphates to produce highly functionalized 1,3-dienes has been developed. This transformation features 1,3-phosphatyloxy group migration followed by 1,3-shifts of bromine and chlorine as well as the unprecedented 1,3-migration of iodine. The reaction is stereodivergent: (Z)-1,3-dienes are formed in the presence of a copper catalyst, whereas gold-catalyzed reactions exhibit inverted stereoselectivity, producing the corresponding E products.

Original languageEnglish (US)
Pages (from-to)6928-6931
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number16
DOIs
StatePublished - Apr 25 2012
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes'. Together they form a unique fingerprint.

  • Cite this