Inter- and intramolecular addition/cyclizations of sulfonamide anions with alkynyliodonium triflates. Synthesis of dihydropyrrole, pyrrole, indole, and tosylenamide heterocycles

Ken S. Feldman, Michelle M. Bruendl, Klaas Schildknegt, Adolph C. Bohnstedt

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94 Scopus citations

Abstract

The synthesis of dihydropyrroles, pyrroles, and indoles through [3-atom + 2-atom] combination of ethyl or aryl tosylamide anions with phenyl(propynyl)iodonium triflate, and the base-mediated intramolecular bicyclization of alkynyliodonium-bearing tosylamide or tosylimide substrates to furnish bicyclic and tricyclic tosylenamide (-enimide) products, is described. A detailed discussion of the scope, limitations, byproduct formation, and the basis for observed diastereoselectivity is presented.

Original languageEnglish (US)
Pages (from-to)5440-5452
Number of pages13
JournalJournal of Organic Chemistry
Volume61
Issue number16
DOIs
StatePublished - Aug 9 1996

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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