Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes

Alexander S. Dudnik, Todd Schwier, Vladimir Gevorgyan

Research output: Contribution to journalArticle

57 Scopus citations

Abstract

A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This domino process involves an unprecedented tandem sequence of 1,3- and 1,2-migrations of two substantially different migrating groups. It is believed that this transformation proceeds via formation of 1,3-diene intermediate or its equivalent, which, upon carbocyclization and aromatization steps, transforms into the naphthalene skeleton. In addition, it was also demonstrated that a variety of 1,3-dienes can be accessed stereoselectively via the 1,3-migration-proton transfer cascade.

Original languageEnglish (US)
Pages (from-to)1859-1870
Number of pages12
JournalTetrahedron
Volume65
Issue number9
DOIs
StatePublished - Feb 28 2009
Externally publishedYes

Keywords

  • 1,3-Dienes
  • Gold
  • Naphthalenes
  • Propargylic esters

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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