Inter-and Intramolecular Addition/Cyclizations of Sulfonamide Anions with Alkynyliodonium Triflates. Synthesis of Dihydropyrrole, Pyrrole, Indole, and Tosylenamide …

KS Feldman, MM Bruendl, K Schildknegt…

Index: Feldman, Ken S.; Bruendl, Michelle M.; Schildknegt, Klaas; Bohnstedt, Adolph C. Journal of Organic Chemistry, 1996 , vol. 61, # 16 p. 5440 - 5452

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Citation Number: 104

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 ...