Anion radical chain cycloaddition of tethered enones: Intramolecular cyclobutanation and Diels-Alder cycloaddition

被引：65

作者：

Roh, Y ^{[1
]}

Jang, HY ^{[1
]}

Lynch, V ^{[1
]}

Bauld, NL ^{[1
]}

Krische, MJ ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 04期

关键词：

D O I：

10.1021/ol0172065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The anion radicals of certain bis(enones), generated by cathodic reduction, are observed to participate in intramolecular cyclobutanation, yielding bicyclo[3.2.0]heptane derivatives through an anion radical chain mechanism. Evidence for stepwise cycloaddition involving distonic anion radical intermediates is presented. In addition to the novel anion radical cyclobutanations, an unprecedented intramolecular anion radical Diets-Alder product is observed. Parallel trends in substrate scope vis-a-vis the Co-catalyzed bis(enone) cyclobutanation are discussed.

引用

页码：611 / 613

页数：3

共 6 条

[1] A diastereoselective metal-catalyzed [2+2] cycloaddition of bis-enones [J].