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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
