The Journal of Organic Chemistry

Formal [3+ 2] cycloaddition of benzylic cations with alkenes

SR Angle, DO Arnaiz

Index: Angle, Steven R.; Arnaiz, Damian O. Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 5937 - 5947

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Citation Number: 65

Abstract

The reaction of benzylic cations with styrenes affords dihydro (1H) indenes in good yield via a formal [3+ 21 atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols.(E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro (W) indenes with three stereogenic centers with> 40: 1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as ...

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