Alkynyliodonium salts in organic synthesis. Preparation of annelated dihydropyrroles by cascade addition/bicyclization of dienyltosylamide anions with phenyl(propynyl)iodonium triflate

Ken S. Feldman, David A. Mareska

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Abstract

The addition of simple pentadienyltosylamide derivatives to the two- carbon electrophile phenyl(propynyl)iodonium triflate initiates a sequence of transformations that furnishes complex, highly functionalized cyclopentenannelated dihydropyrrole products in moderate yields with complete stereoselection. This sequence demonstrates that diyls resulting from homolytic scission of alkylidene carbene-alkene adducts can be readily accessed under mild experimental conditions and that, in the presence of appropriate pendant functionality, these diyls can productively cyclize. The isomeric isoprene-derived tosylamides follow an abbreviated reaction course and deliver azabicyclo[3.1.0]hexanes via an isomerization that competes with diyl formation.

Original languageEnglish (US)
Pages (from-to)5650-5660
Number of pages11
JournalJournal of Organic Chemistry
Volume64
Issue number15
DOIs
Publication statusPublished - Jul 23 1999

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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