Kinetic Separation and Asymmetric Reactions of Norcaradiene Cycloadducts: Facilitated Access via H2O-Accelerated Cycloaddition

Organic Letters
William D Mackay, Jeffrey S Johnson

Abstract

We exploit the Buchner reaction to access 1,2-disubstituted cyclohexadiene synthons (norcaradienes), which participate in H2O-accelerated cycloaddition with dieneophiles to provide cyclopropyl-fused [2.2.2]-bicyclooctene derivatives in good yields. Regioisomeric mixtures can be kinetically separated by exploiting different reaction rates in Diels-Alder reactions. Meso-Diels-Alder products may be enantioselectively desymmetrized, providing highly substituted cyclohexanes with up to seven contiguous stereocenters.

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Citations

Jul 2, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·René PretoriusMartin Albrecht
Sep 20, 2018·Organic & Biomolecular Chemistry·Motoki ItoShigeo Sugiyama
Oct 2, 2019·Angewandte Chemie·Mohanad A HusseinThanh V Nguyen
Feb 19, 2020·Angewandte Chemie·Natalie Holmberg-DouglasDavid A Nicewicz

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