doi: 10.1021/ol400912v.
Epub 2013 Jun 17.
Synthesis of polysubstituted furans via copper-mediated annulation of alkyl ketones with α,β-unsaturated carboxylic acids
Affiliations
- PMID: 23772562
- DOI: 10.1021/ol400912v
Item in Clipboard
Synthesis of polysubstituted furans via copper-mediated annulation of alkyl ketones with α,β-unsaturated carboxylic acids
Org Lett.
.
Abstract
A novel copper-mediated annulation of alkyl ketones with α,β-unsaturated carboxylic acids has been accomplished. This reaction provides a facile and regio-defined method for the synthesis of 2,3,5-trisubstituted furans from simple chemical reagents.
Similar articles
-
Copper-catalyzed regioselective synthesis of furan via tandem cycloaddition of ketone with an unsaturated carboxylic acid under air.Org Biomol Chem. 2015 Jan 7;13(1):309-14. doi: 10.1039/c4ob01320d. Org Biomol Chem. 2015. PMID: 25370303
-
Palladacycle-catalyzed reaction of bicyclic alkenes with terminal ynones: regiospecific synthesis of polysubstituted furans.Org Lett. 2012 Nov 16;14(22):5756-9. doi: 10.1021/ol302586m. Epub 2012 Nov 12. Org Lett. 2012. PMID: 23145937
-
Regioselective Synthesis of Multisubstituted Furans via Copper-Mediated Coupling between Ketones and β-Nitrostyrenes.J Org Chem. 2015 May 15;80(10):5364-8. doi: 10.1021/acs.joc.5b00704. Epub 2015 Apr 30. J Org Chem. 2015. PMID: 25912976
-
Catalytic asymmetric Friedel-Crafts alkylation reactions--copper showed the way.Chem Rev. 2008 Aug;108(8):2903-15. doi: 10.1021/cr078372e. Epub 2008 May 24. Chem Rev. 2008. PMID: 18500844 Review. No abstract available.
-
From micrograms to grams: scale-up synthesis of eribulin mesylate.Nat Prod Rep. 2013 Sep;30(9):1158-64. doi: 10.1039/c3np70051h. Epub 2013 Jul 30. Nat Prod Rep. 2013. PMID: 23896896 Review.
Cited by
-
Rh(III)-catalyzed decarboxylative coupling of acrylic acids with unsaturated oxime esters: carboxylic acids serve as traceless activators.J Am Chem Soc. 2014 Feb 19;136(7):2735-8. doi: 10.1021/ja412444d. Epub 2014 Feb 10. J Am Chem Soc. 2014. PMID: 24512241 Free PMC article.
-
Rhodium(i)-catalyzed C6-selective C-H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids.Chem Sci. 2019 Sep 9;10(43):10089-10096. doi: 10.1039/c9sc03672e. eCollection 2019 Nov 21. Chem Sci. 2019. PMID: 32055363 Free PMC article.
-
Transition-Metal-Free Continuous-Flow Synthesis of 2,5-Diaryl Furans: Access to Medicinal Building Blocks and Optoelectronic Materials.J Org Chem. 2024 Jan 5;89(1):484-497. doi: 10.1021/acs.joc.3c02237. Epub 2023 Dec 24. J Org Chem. 2024. PMID: 38143311 Free PMC article.
-
Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide.Chem Sci. 2021 Dec 6;13(1):241-246. doi: 10.1039/d1sc06403g. eCollection 2021 Dec 22. Chem Sci. 2021. PMID: 35059173 Free PMC article.
-
Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans.Chem Sci. 2021 Oct 27;12(45):15077-15083. doi: 10.1039/d1sc04088j. eCollection 2021 Nov 24. Chem Sci. 2021. PMID: 34909148 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
