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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Diphenylsilylene Transfer to 2-(β-Styryl)benzofurans: Synthesis of Polycyclic Compounds Containing One, Two, or Three
Yoshiki Okamoto1, Takeru Torigoe1, Yoshiyuki Mizuhata2
1Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto606-8585, Japan.
Abstract:
The silylene transfer reaction involving carbon skeletal reorganization is a powerful tool for the production of new silacyclic compounds. However, applicable substrates for this distinctive molecular transformation have been limited to certain conjugated dienes. Herein, we demonstrate that 2-(β-styryl)benzofurans make up a new class of substrates that undergo ring formation with carbon skeletal reorganization in diphenylsilylene transfer from Ph2(Et2N)Si-B(pin). We also report that the resulting 2,3-dihydrosilole derivatives undergo insertion of the second diphenylsilylene into the dearomatized oxacycle.
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