Synthesis of Densely Substituted Trans-Configured 4-Acylated Piperidine-2,4-diones as 3:1 Adducts of Imines and KetenesClick to copy article linkArticle link copied!
Abstract
An operationally simple method is described to form densely substituted diastereomerically pure trans-configured and potentially biologically interesting 5,6-dihydropyridone derivatives as 3:1 adducts of ketenes formed in situ from acyl bromides and aromatic imines.
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This article is cited by 8 publications.
- Xiao-Na Wang, Li-Tao Shen, and Song Ye . NHC-Catalyzed Enantioselective [2 + 2] and [2 + 2 + 2] Cycloadditions of Ketenes with Isothiocyanates. Organic Letters 2011, 13
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- Jesús Manuel Fernández-García, Manuel Á. Fernández-Rodríguez, and Enrique Aguilar . Catalytic Intermolecular Hetero-Dehydro-Diels–Alder Cycloadditions: Regio- and Diasteroselective Synthesis of 5,6-Dihydropyridin-2-ones. Organic Letters 2011, 13
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- Kishor Chandra Bharadwaj, Dharmendra Kumar Tiwari. Double Morita–Baylis–Hillman (MBH) strategy; an intermolecular and a chemo selective intramolecular MBH reactions for 5/6 substituted, functionalized piperidine unit. Tetrahedron 2016, 72
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, 312-317. https://doi.org/10.1016/j.tet.2015.11.041
- Teng-Yue Jian, Xiang-Yu Chen, Li-Hui Sun, Song Ye. N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition of ketenes and 3-aroylcoumarins: highly enantioselective synthesis of dihydrocoumarin-fused dihydropyranones. Org. Biomol. Chem. 2013, 11
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, 158-163. https://doi.org/10.1039/C2OB26804C
- Patrick Meier, Florian Broghammer, Katja Latendorf, Guntram Rauhut, René Peters. Cooperative Al(Salen)-Pyridinium Catalysts for the Asymmetric Synthesis of trans-Configured β-Lactones by [2+2]-Cyclocondensation of Acylbromides and Aldehydes: Investigation of Pyridinium Substituent Effects. Molecules 2012, 17
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, 7121-7150. https://doi.org/10.3390/molecules17067121
- Florian M. Koch, René Peters. Lewis Acid/Base Catalyzed [2+2]‐Cycloaddition of Sulfenes and Aldehydes: A Versatile Entry to Chiral Sulfonyl and Sulfinyl Derivatives. Chemistry – A European Journal 2011, 17
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, 3679-3692. https://doi.org/10.1002/chem.201003542
- Thomas Kull, José Cabrera, René Peters. Catalytic Asymmetric Synthesis of
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‐Configured β‐Lactones: Cooperation of Lewis Acid and Ion Pair Catalysis. Chemistry – A European Journal 2010, 16
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, 9132-9139. https://doi.org/10.1002/chem.201000840
- Radhi. The Investigation of 1H NMR Spectra of 2,3-Dihydro-4-Pyridinones Derived from Bisdemethoxycurcumin. American Journal of Applied Sciences 2010, 7
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, 1053-1056. https://doi.org/10.3844/ajassp.2010.1053.1056
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