Domino reactions consisting of heterocyclization and 1,2-migration-redox-neutral and oxidative transition-metal catalysis |
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| Authors: | Umland Klaus-Daniel Palisse Adeline Haug Timm T Kirsch Stefan F |
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| Affiliation: | 1. Department Chemie, Technische Universit?t München, Lichtenbergstrasse 4, 85747 Garching (Germany);2. New address: Bergische Universit?t Wuppertal, Fachbereich C – Organische Chemie, Gau?stra?e 20, 42119 Wuppertal (Germany) |
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| Abstract: | Two cats, two paths: Two novel domino reactions starting from 6-hydroxy-2-alkyl-2-alkynylcyclohexanones have been discovered. While redox-neutral platinum catalysis gives rise to furans through a sequence of cyclization, 1,2-shift, and Grob fragmentation, oxidative copper catalysis provides an entry to bicyclic 2,3-dihydrofurans. Upon cyclization and oxidation, an unusual benzilic acid rearrangement can take place in this case. |
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| Keywords: | copper domino reactions heterocycles homogeneous catalysis platinum |
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