A novel cascade Pd(II)-catalyzed - cycloisomerization and olefination reaction of 2-benzyl-3-alkynyl chromones with activated/unactivated alkenes has been developed for the synthesis of fused oxatricyclic compounds. This concise one-pot synthetic approach was applied to the difunctionalization of unbiased alkynes based on 2-benzyl-3-(alkynyl)-4-chromen-4-one via -attack - cycloisomerization, followed by olefination with both activated and unactivated alkenes.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.3c02896 | DOI Listing |
Org Lett
January 2025
Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zurich, Switzerland.
We report intramolecular photocatalyzed cycloisomerization of unactivated olefins with pendant nucleophiles. The reaction proceeds under mild conditions and utilizes guanidines, ureas, isoureas, isothioureas, and carbonates to yield several different five-, six-, and seven-membered heterocycles. Use of benzothiazinoquinoxaline as an organophotocatalyst and cobalt-salen catalyst obviates the need for a stoichiometric oxidant or reductant.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Institute of Chemistry, Academia Sinica Taipei, Taiwan, ROC.
Org Lett
August 2024
National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei 112304, Taiwan, R.O.C.
A novel, highly stereoselective gold-catalyzed spirocyclization of 2-benzyl-3-alkynyl chromone with nitrone is described. This cascade reaction involves gold-catalyzed cycloisomerization, nitrone-olefin [3 + 2]-annulation, alkene oxidation, and rearrangement for the formation of spirocyclic products. Interestingly, the isoxazolidine ring generated from [3 + 2]-annulation donates oxygen to alkene to generate a new pyran-3(4)-one and azetidine ring for dispiro-benzofuran formation upon heating.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
May 2024
Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
We report a general, intramolecular cycloisomerization of unactivated olefins with pendant nucleophiles. The reaction proceeds under mild conditions and tolerates ethers, esters, protected amines, acetals, pyrazoles, carbamates, and arenes. It is amenable to N-, O-, as well as C-nucleophiles, yielding a number of different heterocycles including, but not limited to, pyrrolidines, piperidines, oxazolidinones, and lactones.
View Article and Find Full Text PDFOrg Lett
November 2023
National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei 112304, Taiwan, R.O.C.
A novel cascade Pd(II)-catalyzed - cycloisomerization and olefination reaction of 2-benzyl-3-alkynyl chromones with activated/unactivated alkenes has been developed for the synthesis of fused oxatricyclic compounds. This concise one-pot synthetic approach was applied to the difunctionalization of unbiased alkynes based on 2-benzyl-3-(alkynyl)-4-chromen-4-one via -attack - cycloisomerization, followed by olefination with both activated and unactivated alkenes.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!