ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES TO GAMMA-SUBSTITUTED ALLYLIC ALCOHOLS

Authors
YOSHIDA Y UKAJI Y FUJINAMI S INOMATA K
Citation
Y. Yoshida et al., ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES TO GAMMA-SUBSTITUTED ALLYLIC ALCOHOLS, Chemistry Letters, (10), 1998, pp. 1023-1024
Citations number
13
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
10
Year of publication
1998
Pages
1023 - 1024
Database
ISI
SICI code
0366-7022(1998):10<1023:A1CONO>2.0.ZU;2-V
Abstract
The asymmetric 1,3-dipolar cycloaddition of nitrile oxides to gamma-su bstituted allylic alcohols was achieved by the use of diisopropyl (R,R )-tartrate as a chiral auxiliary to afford the corresponding 3,4,5-tri substituted-2-isoxazolines with high regio- and enantioselectivities. 4,5-trans-2-Isaxazolines derived from ethyl (E)-4-hydroxy-2-butenoate were transformed to the corresponding 3,5-cis-2-isoxazolines by the tr eatment with a base through isomerization and lactonization.