Zirconocene-mediated selective c-c bond cleavage of strained carbocycles: Scope and mechanism

Jeffrey Bruffaerts, Alexandre Vasseur, Sukhdev Singh, Ahmad Masarwa, Dorian Didier, Liron Oskar, Lionel Perrin*, Odile Eisenstein, Ilan Marek

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Several approaches using organozirconocene species for the remote cleavage of strained three-membered ring carbocycles are described. ω-Ene polysubstituted cyclopropanes, alkylidenecyclopropanes, ω-ene spiro[2.2]pentanes, and ω-ene cyclopropyl methyl ethers were successfully transformed into stereodefined organometallic intermediates, allowing an easy access to highly stereoenriched acyclic scaffolds in good yields and, in most cases, excellent selectivities. DFT calculations and isotopic labeling experiments were performed to delineate the origin of the obtained chemo- and stereoselectivities, demonstrating the importance of microreversibility.

Original languageAmerican English
Pages (from-to)3497-3515
Number of pages19
JournalJournal of Organic Chemistry
Volume83
Issue number7
DOIs
StatePublished - 6 Apr 2018
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

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