Diasteroselective synthesis of new spiropiperidine scaffolds from the CN(R,S) building block.
A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.
Roulland
Emmanuel
E
Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes (Paris 5), Faculté des Sciences Pharmaceutiques et Biologiques, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
Cecchin
Fabrice
F
Husson
Henri-Philippe
HP
D000470:Alkaloids / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D008094:Lithium / Q000737:chemistry; D018716:Molecular Mimicry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013816:Thermodynamics
D000470:Alkaloids; D009570:Nitriles; D010880:Piperidines; D008094:Lithium