DIASTEREOSELECTIVE PROPIONITRILE OXIDE CYCLOADDITION REACTIONS WITH SOME GAMMA-SUBSTITUTED ALPHA-METHYLENE-GAMMA-BUTYROLACTONES

Authors
PEREIRA SM SAVAGE GP SIMPSON GW GREENWOOD RJ MACKAY MF
Citation
Sm. Pereira et al., DIASTEREOSELECTIVE PROPIONITRILE OXIDE CYCLOADDITION REACTIONS WITH SOME GAMMA-SUBSTITUTED ALPHA-METHYLENE-GAMMA-BUTYROLACTONES, Australian Journal of Chemistry, 46(9), 1993, pp. 1401-1412
Citations number
30
Categorie Soggetti
Chemistry
Journal title
Australian Journal of Chemistry → ACNP
ISSN journal
00049425
Volume
46
Issue
9
Year of publication
1993
Pages
1401 - 1412
Database
ISI
SICI code
0004-9425(1993)46:9<1401:DPOCRW>2.0.ZU;2-L
Abstract
A number of gamma-substituted alpha-methylene-gamma-butyrolactone deri vatives underwent 1,3-dipolar cycloaddition with propionitrile oxide t o give spiro DELTA2-isoxazolines. The reaction proceeded regiospecific ally and with high diastereoselectivity. The products of anti addition predominated. The regiochemistry of addition and relative stereochemi stry of the products were determined by a combination of n.O.e., HETCO R and DOUBTFUL n.m.r. experiments. The assignment was confirmed in one case by X-ray crystallography.