Silver(I)- or copper(II)-mediated dearomatization of aromatic ynones: direct access to spirocyclic scaffolds
- PMID: 25960013
- DOI: 10.1002/anie.201501812
Silver(I)- or copper(II)-mediated dearomatization of aromatic ynones: direct access to spirocyclic scaffolds
Abstract
A high-yielding silver(I)- or copper(II)-catalyzed dearomatizing spirocyclization strategy allows the conversion of simple aromatic compounds that contain ynone substituents, including indole, anisole, pyrrole, and benzofuran derivatives, into functionalized spirocyclic scaffolds. A high-yielding asymmetric variant furnishes spirocyclic indolenines in up to 89:11 e.r.
Keywords: asymmetric catalysis; dearomatization; indolenines; silver; spirocycles.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
Copper-catalyzed oxidative dehydrogenative dearomatization of indole derivatives: A new strategy to construct spirocyclic indolenines.iScience. 2022 Nov 25;25(12):105669. doi: 10.1016/j.isci.2022.105669. eCollection 2022 Dec 22. iScience. 2022. PMID: 36536679 Free PMC article.
-
Copper-Catalyzed Trifluoromethylation of Ynones Coupled with Dearomatizing Spirocyclization of Indoles: Access to CF3-Containing Spiro[cyclopentane-1,3'-indole].Org Lett. 2020 Apr 17;22(8):3291-3296. doi: 10.1021/acs.orglett.0c01097. Epub 2020 Mar 31. Org Lett. 2020. PMID: 32227967
-
Dearomatizing Spiroannulation Reagents: Direct Access to Spirocycles from Indoles and Dihalides.Org Lett. 2018 Jun 1;20(11):3349-3353. doi: 10.1021/acs.orglett.8b01248. Epub 2018 May 10. Org Lett. 2018. PMID: 29745671
-
Application of Metal-Free Dearomatization Reaction as a Sustainable Strategy to Direct Access Complex Cyclic Compounds.Chem Rec. 2023 Oct;23(10):e202300101. doi: 10.1002/tcr.202300101. Epub 2023 May 2. Chem Rec. 2023. PMID: 37132130 Review.
-
Dearomatizing benzene ring reductases.J Mol Microbiol Biotechnol. 2005;10(2-4):132-42. doi: 10.1159/000091560. J Mol Microbiol Biotechnol. 2005. PMID: 16645310 Review.
Cited by
-
Visible-light-induced intramolecular charge transfer in the radical spirocyclisation of indole-tethered ynones.Chem Sci. 2019 Dec 13;11(5):1353-1360. doi: 10.1039/c9sc05311e. Chem Sci. 2019. PMID: 34123259 Free PMC article.
-
From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis.Chemistry. 2016 May 4;22(19):6496-500. doi: 10.1002/chem.201600823. Epub 2016 Mar 23. Chemistry. 2016. PMID: 26918778 Free PMC article.
-
A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines.Org Lett. 2021 Mar 19;23(6):2063-2068. doi: 10.1021/acs.orglett.1c00205. Epub 2021 Mar 1. Org Lett. 2021. PMID: 33645997 Free PMC article.
-
Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones.Chemistry. 2016 Jun 20;22(26):8777-80. doi: 10.1002/chem.201601836. Epub 2016 May 19. Chemistry. 2016. PMID: 27124236 Free PMC article.
-
Substrate-Controlled Product Divergence: Silver-Catalyzed Reaction of Trifluoromethyl Ketones with Terminal Alkynes.ACS Omega. 2017 Mar 22;2(3):1104-1115. doi: 10.1021/acsomega.6b00432. eCollection 2017 Mar 31. ACS Omega. 2017. PMID: 31457493 Free PMC article.
LinkOut - more resources
Full Text Sources