SYNTHESIS, STRUCTURE AND CHIROPTICAL PROPERTIES OF ISOXAZOLIDIN-5-ONES

Authors
FRELEK J PANFIL I GLUZINSKI P CHMIELEWSKI M
Citation
J. Frelek et al., SYNTHESIS, STRUCTURE AND CHIROPTICAL PROPERTIES OF ISOXAZOLIDIN-5-ONES, Tetrahedron : asymmetry, 7(12), 1996, pp. 3415-3426
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
12
Year of publication
1996
Pages
3415 - 3426
Database
ISI
SICI code
0957-4166(1996)7:12<3415:SSACPO>2.0.ZU;2-1
Abstract
Several isoxazolidin-5-ones were synthesized in an addition - rearrang ement reaction from corresponding sugar lactones and hydroxylamines. T he sign of the Cotton effect at ca. 220 nm can be correlated to the ab solute configuration of the stereogenic center at C3 and can be predic ted by Weigang's sector rule. X-ray diffraction study performed for 11 and 12 confirms the configuration at C3 to be 3S and 3R, respectively . Copyright (C) 1996 Elsevier Science Ltd