Unprecedented regio- and stereoselective conversion of 1-cyclopropyl-3-ethoxycyclopentadienes to 3-(E)-alkylidenecyclopentenes

被引：13

作者：

Flynn, BL ^{[1
]}

de Meijere, A ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 02期

关键词：

D O I：

10.1021/jo980938z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopropylalkynes 1 were converted into cyclopropyl-substituted 3-ethoxy-5-dimethylaminocyclopentadienes 4 via initially formed (beta-dimethylaminoethenyl)carbene complexes 3 and their subsequent-formal [3 + 2] cycloaddition to a second alkyne of type 1 (overall yields 51-59%). New regio- and stereoselective 1,7-addition and 1,6-substitution reactions have been developed that convert cyclopentadienes 4 into highly functionalized cyclopentenes 5 and 11, respectively (yields 98-99% and 61%, respectively). An in situ domino reaction consisting of a [3 + 2] cycloaddition and subsequent 1,7-addition has also been achieved (86% overall yield).

引用

页码：400 / 404

页数：5

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