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

被引：103

作者：

Feldman, KS

Bruendl, MM

Schildknegt, K

Bohnstedt, AC

机构：

[1] Department of Chemistry, Pennsylvania State University, University Park

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 16期

关键词：

D O I：

10.1021/jo9605814

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5440 / 5452

页数：13

共 43 条

[41] A NEW METHOD FOR THE SYNTHESIS OF CYCLOPENTENONES VIA THE TANDEM MICHAEL ADDITION-CARBENE INSERTION REACTION OF BETA-KETOETHYNYL(PHENYL)IODONIUM SALTS [J].