A NOVEL HETERO-DIELS-ALDER APPROACH TOWARDS PERHYDROQUINOLINONES BEARING AN ANGULAR METHYL-GROUP

Authors
STANETTY P MIHOVILOVIC MD MEREITER K VOLLENKLE H RENZ F
Citation
P. Stanetty et al., A NOVEL HETERO-DIELS-ALDER APPROACH TOWARDS PERHYDROQUINOLINONES BEARING AN ANGULAR METHYL-GROUP, Tetrahedron, 54(5-6), 1998, pp. 875-894
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
5-6
Year of publication
1998
Pages
875 - 894
Database
ISI
SICI code
0040-4020(1998)54:5-6<875:ANHATP>2.0.ZU;2-O
Abstract
The title compounds 9-11 were synthesized by a hetero Diels-Alder reac tion using the sterically demanding diene 2 as a new building block. T he effect of commonly used Lewis acids and the substitution pattern of various imines 5 on both the mechanism and the diastereoselectivity o f the reaction with the diene is discussed and compared with data obta ined by ab initio calculations. (C) 1997 Elsevier Science Ltd. All rig hts reserved.