TY - JOUR
T1 - Inter- and intramolecular addition/cyclizations of sulfonamide anions with alkynyliodonium triflates. Synthesis of dihydropyrrole, pyrrole, indole, and tosylenamide heterocycles
AU - Feldman, Ken S.
AU - Bruendl, Michelle M.
AU - Schildknegt, Klaas
AU - Bohnstedt, Adolph C.
PY - 1996/8/9
Y1 - 1996/8/9
N2 - 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.
AB - 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.
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U2 - 10.1021/jo9605814
DO - 10.1021/jo9605814
M3 - Article
AN - SCOPUS:0001459832
SN - 0022-3263
VL - 61
SP - 5440
EP - 5452
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -