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.
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页码：5937 / 5947
页数：11
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