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.
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页码：5440 / 5452
页数：13
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