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Taming of Furfurylidenes by Chiral Bismuth-Rhodium Paddlewheel Catalysts. Preparation and Functionalization of Optically Active 1,1-Disubstituted (Trifluoromethyl)cyclopropanes

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Peeters,  Matthias
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Decaens,  Jonathan
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

443_anie202311598-s1-si_cf3-cyclopropanes_v2.pdf
(Supplementary material), 8MB

Citation

Peeters, M., Decaens, J., & Fürstner, A. (2023). Taming of Furfurylidenes by Chiral Bismuth-Rhodium Paddlewheel Catalysts. Preparation and Functionalization of Optically Active 1,1-Disubstituted (Trifluoromethyl)cyclopropanes. Angewandte Chemie International Edition, 62(44): e202311598. doi:10.1002/anie.202311598.


Cite as: https://hdl.handle.net/21.11116/0000-000D-D415-C
Abstract
Although 2-furyl-carbenes (furfurylidenes) are prone to instantaneous electrocyclic ring opening, chiral [BiRh]-paddlewheel complexes empowered by London dispersion allow (trifluoromethyl)furfurylidene metal complexes to be generated from a bench-stable triftosylhydrazone precursor. These reactive intermediates engage in asymmetric [2+1] cycloadditions and hence open entry into valuable trifluoromethylated cyclopropane or −cyclopropene in optically active form, which are important building blocks for medicinal chemistry but difficult to make otherwise.