CYCLOADDITIONS .51. STEREOSELECTIVE FORMATION OF FUNCTIONALIZED 2-ARYL-TETRAHYDROFURANS FROM AROMATIC-ALDEHYDES VIA INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITIONS (INOC AND IOOC)

Authors
HASSNER A RAI KML DEHAEN W
Citation
A. Hassner et al., CYCLOADDITIONS .51. STEREOSELECTIVE FORMATION OF FUNCTIONALIZED 2-ARYL-TETRAHYDROFURANS FROM AROMATIC-ALDEHYDES VIA INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITIONS (INOC AND IOOC), Synthetic communications, 24(12), 1994, pp. 1669-1682
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
24
Issue
12
Year of publication
1994
Pages
1669 - 1682
Database
ISI
SICI code
0039-7911(1994)24:12<1669:C.SFOF>2.0.ZU;2-5
Abstract
Alpha-Allyloxyaldoximes 8, formed by the reduction of beta-nitrostyren es 5 with SnCl2-2H2O in the presence of an unsaturated alcohol, underg o either thermally induced intramolecular oxime olefin cycloaddition ( IOOC) to bicyclic isoxazolidines 7, with stereospecific introduction o f three stereocenters, of nitrile oxide olefin cycloadditions (INOC) t o bicyclic isoxazolines 6 This provides an entry into functionalized t etrahydrofurans and tetrahydropyrans.