Formation of seven- and eight-membered rings by manganese (III)-based oxidative free radical cyclization. |
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| Affiliation: | 1. School of Chemistry, University of Bristol, Cantock''s Close, Bristol BS8 1TS, United Kingdom;2. Engineering of Molecular NanoSystems, Ecole Polytechnique de Bruxelles, Université Libre de Bruxelles, Avenue F.D. Roosevelt 50, CP165/64, B-1050 Brussels, Belgium;1. Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Hyderabad 500049, India;2. Department of Organic Chemistry, Foods, Drugs and Water, Andhra University, Visakhapatnam 530003, India;1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation;2. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, Moscow 119991, Russian Federation;1. N.S. Enikolopov Institute of Synthetic Polymer Materials, Russian Academy of Science, 117393 Moscow, Profsoyuznaya st. 70, Russia;2. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Science, 119991 Moscow, Vavilova st. 28, Russia |
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| Abstract: | Oxidative free radical cyclizations of β-ketoesters 1, 5, 11, and 14 with Mn(OAc)3·2H2O and Cu(OAc)2·H2O proceed in moderate yield to give seven- and eight-membered rings. The regiochemistry of the cyclization and oxidative termination are described. |
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