Formal [4+4]-, [4+3]-, and [4+2]-Cycloaddition Reactions of Donor-Acceptor Cyclobutenes, Cyclopropenes and Siloxyalkynes Induced by Brønsted Acid Catalysis

Date
2021-02-18
Authors
Doyle, Michael
Zheng, Haifeng
Wang, Rui
Wang, Kan
Wherritt, Daniel J.
Arman, Hadi
Journal Title
Journal ISSN
Volume Title
Publisher
Royal Society of Chemistry
Abstract

Brønsted acid catalyzed formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloadditions of donor–acceptor cyclobutenes, cyclopropenes, and siloxyalkynes with benzopyrylium ions are reported. [4 + 2]-cyclization/deMayo-type ring-extension cascade processes produce highly functionalized benzocyclooctatrienes, benzocycloheptatrienes, and 2-naphthols in good to excellent yields and selectivities. Moreover, the optical purity of reactant donor–acceptor cyclobutenes is fully retained during the cascade. The 1,3-dicarbonyl product framework of the reaction products provides opportunities for salen-type ligand syntheses and the construction of fused pyrazoles and isoxazoles that reveal a novel rotamer-diastereoisomerism.

Description
Keywords
Citation
10.1039/d1sc00158b
Department
Chemistry