Herein we have developed the silver-catalyzed electronic- and steric-controlled intramolecular formal [2 + 2]-cycloaddition of alkyne-tethered cyclohexadienones. Substrates with electron-rich alkynes and a less hindered quaternary carbon center afford tricyclic fused cyclobutenes through 1,7-enyne cyclization. In contrast, the formation of dihydrofurans was observed from electron-deficient alkynes via proton abstraction/C-O bond cleavage. The synthetic potential of this method was also broadened with a gram-scale reaction and various transformations on cyclobutene.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.1c04232 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Steric- and Electronic-Controlled Intramolecular [2 + 2]-Cycloaddition of Cyclohexadienone-Containing 1,7-Enynes.
Org Lett
January 2022
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
Herein we have developed the silver-catalyzed electronic- and steric-controlled intramolecular formal [2 + 2]-cycloaddition of alkyne-tethered cyclohexadienones. Substrates with electron-rich alkynes and a less hindered quaternary carbon center afford tricyclic fused cyclobutenes through 1,7-enyne cyclization. In contrast, the formation of dihydrofurans was observed from electron-deficient alkynes via proton abstraction/C-O bond cleavage.
View Article and Find Full Text PDFIntegrating Metal-Catalyzed C-H and C-O Functionalization To Achieve Sterically Controlled Regioselectivity in Arene Acylation.
J Am Chem Soc
August 2018
Department of Chemistry , University of Minnesota-Twin Cities, 207 Pleasant Street SE , Minneapolis , Minnesota 55455 , United States.
One major goal of organometallic chemists is the direct functionalization of the bonds most recurrent in organic molecules: C-H, C-C, C-O, and C-N. An even grander challenge is C-C bond formation when both precursors are of this category. Parallel to this is the synthetic goal of achieving reaction selectivity that contrasts with conventional methods.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!