Formal [4+4]-, [4+3]-, and [4+2]-Cycloaddition Reactions of Donor-Acceptor Cyclobutenes, Cyclopropenes and Siloxyalkynes Induced by Brønsted Acid Catalysis
| dc.contributor.author | Doyle, Michael | |
| dc.contributor.author | Zheng, Haifeng | |
| dc.contributor.author | Wang, Rui | |
| dc.contributor.author | Wang, Kan | |
| dc.contributor.author | Wherritt, Daniel J. | |
| dc.contributor.author | Arman, Hadi | |
| dc.date.accessioned | 2021-11-15T18:41:12Z | |
| dc.date.available | 2021-11-15T18:41:12Z | |
| dc.date.issued | 2021-02-18 | |
| dc.description.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. | en_US |
| dc.description.department | Chemistry | en_US |
| dc.identifier.citation | 10.1039/d1sc00158b | en_US |
| dc.identifier.issn | 2041-6539 | |
| dc.identifier.uri | https://hdl.handle.net/20.500.12588/714 | |
| dc.language.iso | en_US | en_US |
| dc.publisher | Royal Society of Chemistry | en_US |
| dc.relation.ispartofseries | Chemical Science; | |
| dc.rights | Attribution 3.0 United States | * |
| dc.rights.uri | http://creativecommons.org/licenses/by/3.0/us/ | * |
| dc.title | Formal [4+4]-, [4+3]-, and [4+2]-Cycloaddition Reactions of Donor-Acceptor Cyclobutenes, Cyclopropenes and Siloxyalkynes Induced by Brønsted Acid Catalysis | en_US |
| dc.type | Article | en_US |