ENANTIOSELECTIVE CU-CATALYZED 1,4-ADDITION OF ME(3)AL TO A 4,4-DISUBSTITUTED CYCLOHEXA-2,5-DIENONE

Authors
TAKEMOTO Y KURAOKA S HAMAUE N AOE K HIRAMATSU H IWATA C
Citation
Y. Takemoto et al., ENANTIOSELECTIVE CU-CATALYZED 1,4-ADDITION OF ME(3)AL TO A 4,4-DISUBSTITUTED CYCLOHEXA-2,5-DIENONE, Tetrahedron, 52(45), 1996, pp. 14177-14188
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
45
Year of publication
1996
Pages
14177 - 14188
Database
ISI
SICI code
0040-4020(1996)52:45<14177:EC1OMT>2.0.ZU;2-X
Abstract
A series of chiral enantiomerically pure 2-aryloxazolines was synthesi zed 4S)-2-(2',6'-dimethoxyphenyl)-4-isopropyloxazoline proved to be an efficient chiral ligand for the Cu-catalyzed conjugate addition of Me (3)Al to cyclohexadienone, and by using 20mol% of this ligand 1,4-addu ct was obtained in 68% ee. In addition, TBDMSOTf is crucial for the as ymmetric conjugate addition to proceed with good chemical yield and hi gh ee. Copyright (C) 1996 Elsevier Science Ltd