Ortho-quinone methides as reactive intermediates in asymmetric brønsted Acid catalyzed cycloadditions with unactivated alkenes by exclusive activation of the electrophile

Angewandte Chemie
Chien-Chi HsiaoMagnus Rueping

Abstract

An efficient method for the highly enantioselective synthesis of chiral chromanes bearing multiple stereogenic centers was developed. A chiral BINOL-based N-triflylphosphoramide proved to be an effective catalyst for the in situ generation of ortho-quinone methides (o-QMs) and their subsequent cycloaddition reaction with unactivated alkenes provided chromanes with excellent diastereo- and enantioselectivity.

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Citations

Sep 26, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Felix E HeldSvetlana B Tsogoeva
Jun 30, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lorenzo CaruanaLuca Bernardi
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May 4, 2018·Chemistry : a European Journal·Hsuan-Hung LiaoMagnus Rueping
Mar 5, 2016·Organic & Biomolecular Chemistry·Yuk Fai WongJianwei Sun
Oct 3, 2018·Chemical Communications : Chem Comm·Renjie ChenSunliang Cui

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