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Paper | Special issue | Vol 47, No. 2, 1998, pp.747-755
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)60
A Novel Route to Chiral Non Racemic 2-Substituted 1,2,3,4-Tetrahydroquinolines

Marie-Christine Lallemand, Mathieu Gaillard, Nicole Kunesch,* and Henri-Philippe Husson*

*CNRS-URA 1310, Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes, 4, avenue de l'Observatoire, 75270 Pairs Cedex 06, France

Abstract

The chiral non racemic α-cyanopiperidine (1) and its α-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.