HIGH-PRESSURE DIELS-ALDER REACTIONS OF 1-VINYL-2,2,6-TRIMETHYLCYCLOHEXENE CATALYZED BY CHIRAL LEWIS-ACIDS - AN ENANTIOSELECTIVE ROUTE TO A DRIMANE SESQUITERPENE PRECURSOR

Authors
KNOL J MEETSMA A FERINGA BL
Citation
J. Knol et al., HIGH-PRESSURE DIELS-ALDER REACTIONS OF 1-VINYL-2,2,6-TRIMETHYLCYCLOHEXENE CATALYZED BY CHIRAL LEWIS-ACIDS - AN ENANTIOSELECTIVE ROUTE TO A DRIMANE SESQUITERPENE PRECURSOR, Tetrahedron : asymmetry, 6(5), 1995, pp. 1069-1072
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
5
Year of publication
1995
Pages
1069 - 1072
Database
ISI
SICI code
0957-4166(1995)6:5<1069:HDRO1>2.0.ZU;2-1
Abstract
The Diels Alder reaction of 1-vinyl-2,2,6-trimethylcyclohexene 4 and 3 -(methoxycarbonyl)propenoyl)-1,3-oxazolidin-2-one 5 under high pressur e, catalyzed by a chiral bis-imine copper(II) complex, yields a driman e sesquiterpene precursor in a highly regio- and diastereoselective ma nner with enantioselectivities up to 64%; nearly enantiomerically pure material is obtained by one simple crystallization.