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Regio- and diastereoselectivity of the cycloaddition of aldonitrones with benzylidenecyclopropane: An experimental and theoretical study |
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| Authors: | Ekaterina V. Sirotkina Mariia M. Efremova Alexander S. Novikov Vladimir V. Zarubaev Iana R. Orshanskaya Galina L. Starova Rafael R. Kostikov Alexander P. Molchanov |
| Affiliation: | 1. Saint-Petersburg State University, Universitetskaya nab. 7/9, St-Petersburg, 199034, Russian Federation;2. Influenza Research Institute, St. Petersburg, Russian Federation |
| Abstract: | 1,3-Dipolar cycloaddition of benzylidenecyclopropane with various aldonitrones proceeds regioselectively giving good yields of 4-spirocyclopropane isoxazolidines. In the case of aldonitrones, bearing carbamoyl- or aryl-groups on the carbon atom, only the cis-isomer is formed. The compounds synthesized were tested for their virus-inhibiting activity. |
| Keywords: | Benzylidenecyclopropane Nitrones Cycloaddition Selectivity DFT calculations |
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