STEREOSELECTIVE CYCLOADDITION OF NITRILE OXIDES TO A DISPIROKETAL-PROTECTED BUT-3-ENE-1,2-DIOL

Authors
GRAVESTOCK MB PATON RM TODD CJ
Citation
Mb. Gravestock et al., STEREOSELECTIVE CYCLOADDITION OF NITRILE OXIDES TO A DISPIROKETAL-PROTECTED BUT-3-ENE-1,2-DIOL, Tetrahedron : asymmetry, 6(11), 1995, pp. 2723-2730
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
11
Year of publication
1995
Pages
2723 - 2730
Database
ISI
SICI code
0957-4166(1995)6:11<2723:SCONOT>2.0.ZU;2-T
Abstract
The influence of a dispiroketal protecting group on the pi-facial sele ctivity of nitrile oxide cycloaddition to S-but-3-ene-1,2-diol has bee n investigated Ethoxycarbonylformonitrile oxide and benzonitrile oxide undergo regiospecific and diasteroeselective addition to alkene 7 to afford isoxazolines 11 and 12. The major adducts (11a and 11b) are for med with 44% and 50% d.e. respectively, and in each case have S-config uration at C-5, the new stereogenic centre.