FORMAL [3 + 2] CYCLOADDITION OF BENZYLIC CATIONS WITH ALKENES

被引：79

作者：

ANGLE, SR

ARNAIZ, DO

机构：

[1] Department of Chemistry, University of California, Riverside

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 22期

关键词：

D O I：

10.1021/jo00048a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.

引用

页码：5937 / 5947

页数：11

共 63 条

[1] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].