Reductive and Oxidative Transformations of the N-(Cyanomethyl)oxazolidine System to Expand the Chiral Pool of Piperidines

Reductive and Oxidative Transformations of the N-(Cyanomethyl)oxazolidine System to Expand the Chiral Pool of Piperidines

Two new reactions have been exploited to modify piperidine scaffolds containing the chiral, non‐racemic N‐(cyanomethyl)oxazolidine system. A Raney nickel mediated decyanation was studied first, followed by an oxidative process using potassium permanganate to furnish enantiopure lactams including oxo...

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Veröffentlicht in:European journal of organic chemistry 2004-12, Vol.2004 (23), p.4823-4829
Hauptverfasser: François, David, Poupon, Erwan, Kunesch, Nicole, Husson, Henri-Philippe
Format: Artikel
Sprache:eng
Schlagworte:
Chirality
Lactams
Piperidines
Potassium permanganate
Raney nickel
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Zusammenfassung:Two new reactions have been exploited to modify piperidine scaffolds containing the chiral, non‐racemic N‐(cyanomethyl)oxazolidine system. A Raney nickel mediated decyanation was studied first, followed by an oxidative process using potassium permanganate to furnish enantiopure lactams including oxopipecolic acid derivatives. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400404