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.

An enantiospecific entry to fluoro substituted aminocyclopentanols through intramolecular nitrile oxide, nitrone, and oxime cycloaddition reactions

RESNATI, GIUSEPPE
1994-01-01

Abstract

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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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/655559
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