Diasteroselective synthesis of new spiropiperidine scaffolds from the CN(R,S) building block.

Autor: Roulland 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 F, Husson HP
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2005 May 27; Vol. 70 (11), pp. 4474-7.
DOI: 10.1021/jo050258d
Abstrakt: 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.
Databáze: MEDLINE