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Organolithium-induced synthesis of acyclic unsaturated amino alcohols from epoxides of dihydropyrroles and tetrahydropyridines |
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| Authors: | David M Hodgson Timothy J MilesJason Witherington |
| Institution: | a The Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford OX1 3QY, UK b Neurology and GI Centre of Excellence for Drug Discovery, GlaxoSmithKline Research Limited, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, UK |
| Abstract: | The alkylative double ring-opening of Bus-protected 2,5-dihydropyrrole epoxides 13 and 29 with organolithiums to give 3-substituted 1-aminobut-3-en-2-ols 13-19 and 30-32 are described. Bus-protected tetrahydropyridine epoxide 38 reacts with organolithiums to give 4-substituted 1-aminobut-4-en-3-ols 39 and tetrahydropyridinol 40. |
| Keywords: | epoxides organolithiums amino alcohols eliminations and alkenes |
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