Substrate-Controlled [8 + 3] Cycloaddition of Tropsulfimides and Tropones with Zwitterionic Allenyl Palladium Species Derived from Vinylidenecyclopropane-diesters.

Autor: Long YJ; State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China., Shen JH; State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China., Wei Y; State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China., Shi M; State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Oct 18; Vol. 89 (20), pp. 14831-14850. Date of Electronic Publication: 2024 Oct 04.
DOI: 10.1021/acs.joc.4c01579
Abstrakt: A palladium-catalyzed regioselective [8 + 3] cycloaddition of tropsulfimides and tropones with vinylidenecyclopropane-diesters (VDCP-diesters) has been disclosed in this paper, affording decahydro-1 H -cyclohepta[ b ]pyridine derivatives bearing an allene moiety or decahydro-1 H -cyclohepta[ b ]pyran derivatives having a conjugated diene unit in moderate to good yields. The reactions proceed through a zwitterionic allenyl palladium species derived from VDCP-diesters. The substrate scopes have been investigated and the plausible reaction mechanisms have also been proposed according to the previous work, the first captured zwitterionic Pd-allenyl intermediate, and control experiments.
Databáze: MEDLINE
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