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The diastereoselective synthesis of functionalised isoxazolidines using a Cope elimination/intramolecular nitrone cycloaddition strategy |
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| Authors: | Ian A O'Neil VElena Ramos Ed Cleator David J Tapolczay |
| Institution: | a Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Crown Street, Liverpool L69 7ZD, UK b Millennium Pharmaceuticals, 75, Sidney Street, Cambridge, MA, USA c James Black Foundation, 68, Half Moon Lane, Dulwich, London SE24 9JE, UK |
| Abstract: | Functionalised hydroxylamine derivatives of (S)-prolinol prepared by a Cope elimination have been found to undergo oxidation to the nitrone either in the presence of air or a catalytic quantity of TPAP. These undergo intramolecular cycloaddition to give tricyclic isoxazolidines with high diastereoselectivity. |
| Keywords: | Cope elimination Nitrones Cycloaddition |
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