Starting from (2R,3S)-2-benzyloxy-3-fluoro-5-hexenale 2 and its (2R,3R) epimer, cyclopentanoisoxazolidines 4 and 7 are obtained with complete diastereoselectivity through nitrone and oxime intiainolecular cycloaddition reactions. In contrast, cyclopentanoisoxazolines 6 are formed with only medium stereoselectivily through intramolecular nitrile oxide cycloaddition reactions. Further elaboration of these bicyclic compounds affords fluoro substituted aminocyclopetanols 8 and 10 in enantiomerically and diastereoisomerically pure form. 2-Hydroxy-3-fluoro-5-hydroxymethylcyclopentyl amine 10 and corresponding cyclic analogues 8, which are structurally similar to some glycosidase inhibitors, have been prepared in enantiomerically and diastereoisomerically pure form.
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