A NOVEL ROUTE TO CHIRAL NON RACEMIC 2-SUBSTITUTED 1,2,3,4-TETRAHYDROQUINOLINES

Authors
LALLEMAND MC GAILLARD M KUNESCH N HUSSON HP
Citation
Mc. Lallemand et al., A NOVEL ROUTE TO CHIRAL NON RACEMIC 2-SUBSTITUTED 1,2,3,4-TETRAHYDROQUINOLINES, Heterocycles, 47(2), 1998, pp. 747-755
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
47
Issue
2
Year of publication
1998
Pages
747 - 755
Database
ISI
SICI code
0385-5414(1998)47:2<747:ANRTCN>2.0.ZU;2-W
Abstract
The chiral non racemic alpha-cyanopiperidine (1) and its alpha-methyl derivative (4) react with activated alkynes. Depending on the reaction conditions, Michael adducts are obtained. Moreover, synthon (4) gives access to the 1,2,3,4-tetrahydroquinoline framework in one step. The substitution pattern on the aromatic ring depends on the alkyne. This constitutes a new and short synthetic method of chiral non racemic 1,2 ,3,4-tetrahydroquinolines.