AN ENANTIOSPECIFIC ENTRY TO FLUORO SUBSTITUTED AMINOCYCLOPENTANOLS THROUGH INTRAMOLECULAR NITRILE OXIDE, NITRONE, AND OXIME CYCLOADDITION REACTIONS

Authors
ARNONE A CAVICCHIOLI M DONADELLI A RESNATI G
Citation
A. Arnone et al., AN ENANTIOSPECIFIC ENTRY TO FLUORO SUBSTITUTED AMINOCYCLOPENTANOLS THROUGH INTRAMOLECULAR NITRILE OXIDE, NITRONE, AND OXIME CYCLOADDITION REACTIONS, Tetrahedron : asymmetry, 5(6), 1994, pp. 1019-1028
Citations number
43
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
6
Year of publication
1994
Pages
1019 - 1028
Database
ISI
SICI code
0957-4166(1994)5:6<1019:AEETFS>2.0.ZU;2-T
Abstract
Starting from (2R,3S)-2-benzyloxy-3-fluoro-5-hexenale 2 and its (2R,3R ) epimer, cyclopentanoisoxazolidines 4 and 7 are obtained with complet e diastereoselectivity through nitrone and oxime intramolecular cycloa ddition reactions. In contrast, cyclopentanoisoxazolines 6 are formed with only medium stereoselectivity through intramolecular nitrile oxid e cycloaddition reactions. Further elaboration of these bicyclic compo unds affords fluoro substituted aminocyclopetanols 8 and 10 in enantio merically and diastereoisomerically pure form.