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- Title
Synthesis of 7-Membered Ring Carbocycles via a Palladium-Catalyzed Intramolecular Allylic Alkylation–Isomerization–Cope Rearrangement Cascade.
- Authors
Tsuruda, Kazuki; Tokumoto, Takahisa; Inoue, Naoya; Nakajima, Masaya; Nemoto, Tetsuhiro
- Abstract
We developed a novel method for synthesizing seven-membered ring carbocycles via a palladium-catalyzed intramolecular allylic alkylation–isomerization–Cope rearrangement cascade. Using easily available lactone derivatives as substrates, the target cascade reaction proceeded in the presence of 5 mol-% of Pd(dba)2 and 6 mol-% of 1,3-diphenylphosphinopropane (dppp) in THF, affording a series of seven-memberedring carbocycles in 59–88 % yield (11 examples). DFT calculations suggested that, in addition to the reaction cascade including the cis-divinylcyclopropane Cope rearrangement, there is another possible pathway based on the palladium-catalyzed intramolecular allylic substitution to construct the seven-membered ring through a retro-cyclopropanation-mediated oxidative addition.
- Subjects
CARBOCYCLIC compounds; PALLADIUM catalysts; ALLYLIC alkylation; ISOMERIZATION; REARRANGEMENTS (Chemistry); CHEMICAL synthesis
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 22, p2836
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201800230