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

doi:10.1021/jo9605814

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

Chemistry

Research output: Contribution to journal › Article › peer-review

109 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 language	English (US)
Pages (from-to)	5440-5452
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	61
Issue number	16
DOIs	https://doi.org/10.1021/jo9605814
State	Published - Aug 9 1996

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo9605814

Cite this

@article{07fa4e9925044ca2a2915fd402aa0396,

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

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.",

author = "Feldman, \{Ken S.\} and Bruendl, \{Michelle M.\} and Klaas Schildknegt and Bohnstedt, \{Adolph C.\}",

year = "1996",

month = aug,

day = "9",

doi = "10.1021/jo9605814",

language = "English (US)",

volume = "61",

pages = "5440--5452",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "16",

}

Inter- and intramolecular addition/cyclizations of sulfonamide anions with alkynyliodonium triflates. Synthesis of dihydropyrrole, pyrrole, indole, and tosylenamide heterocycles. / Feldman, Ken S.; Bruendl, Michelle M.; Schildknegt, Klaas et al.
In: Journal of Organic Chemistry, Vol. 61, No. 16, 09.08.1996, p. 5440-5452.

Research output: Contribution to journal › Article › peer-review

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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UR - https://www.scopus.com/pages/publications/0001459832#tab=citedBy

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 -

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

Abstract

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