Journal of Organic Chemistry p. 5937 - 5947 (1992)
Update date:2022-09-26
Topics:
Angle, Steven R.
Arnaiz, Damian O.
The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal <3+2> atom cycloadditon.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 methylcyclohexane afforded cycloadducts in 66percent and 51percent yields, respectively.
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