Asymmetric,Three‐Component,One‐Pot Synthesis of Spiropyrazolones and 2,5‐Chromenediones from Aldol Condensation/NHC‐Catalyzed Annulation Reactions |
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| Authors: | Dr. Lei Wang Sun Li Dr. Pankaj Chauhan Dr. Daniel Hack Arne R. Philipps Dr. Rakesh Puttreddy Prof. Dr. Kari Rissanen Prof. Dr. Gerhard Raabe Prof. Dr. Dieter Enders |
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| Affiliation: | 1. Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany;2. Department of Chemistry, Nanoscience Center, University of Jyvaskyla, JYU, Finland |
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| Abstract: | A novel one‐pot, three‐component diastereo‐ and enantioselective synthesis of spiropyrazolones has been developed involving the aldol condensation of an enal to generate α,β‐unsaturated pyrazolones, which react with a second equivalent of enal through an N‐heterocyclic carbene (NHC)‐catalyzed [3+2] annulation. The desired spirocyclopentane pyrazolones are obtained in moderate to good yields and good to excellent stereoselectivities. Alternatively, starting from cyclic 1,3‐diketones, 2,5‐chromenediones are available through [2+4] annulation. |
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| Keywords: | asymmetric synthesis chromenedione multicomponent reaction N-heterocyclic carbene spiropyrazolone |
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