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Zirconocene-Mediated Selective C–C Bond Cleavage of Strained Carbocycles: Scope and Mechanism

Abstract : Several approaches using organozirconocene species for the remote cleavage of strained three-membered ring carbocycles such as w-ene polysubstituted cyclopropanes, alkylidenecyclopropanes, w-ene spiro[2.2]pentanes and wene cyclopropyl methyl ethers, into stereodefined organometallic intermediates were successfully developed to access highly stereoenriched scaffolds in good yields. Two acyclic stereocenters including a quaternary carbon stereogenic carbon atom were easily obtained with very high diastereoselectivities. DFT calculations and isotopic labeling experiments were performed to delineate the origin of the observed stereoselectivities.
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https://hal.archives-ouvertes.fr/hal-03770459
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Submitted on : Tuesday, September 6, 2022 - 5:19:57 PM
Last modification on : Tuesday, October 25, 2022 - 4:14:09 AM

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Jeffrey Bruffaerts, Alexandre Vasseur, Sukhdev Singh, Ahmad Masarwa, Dorian Didier, et al.. Zirconocene-Mediated Selective C–C Bond Cleavage of Strained Carbocycles: Scope and Mechanism. Journal of Organic Chemistry, 2018, 83 (7), pp.3497-3515. ⟨10.1021/acs.joc.7b03115⟩. ⟨hal-03770459⟩

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