New Piperidine Scaffolds via Nucleophilic Reactivity of (−)-Phenyloxazolopiperidine

New Piperidine Scaffolds via Nucleophilic Reactivity of (−)-Phenyloxazolopiperidine

The present work illustrates the power of compound 2 as a chiral, nonracemic, and stable 2-piperideine (enamine) equivalent in the rapid and efficient construction of 3-substituted piperidines (carbon−carbon and carbon−sulfur bonds) such as 3-spiropiperidines. This methodology offers a new route to...

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Veröffentlicht in:Journal of organic chemistry 2004-05, Vol.69 (11), p.3836-3841
Hauptverfasser: Poupon, Erwan, François, David, Kunesch, Nicole, Husson, Henri-Philippe
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
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Zusammenfassung:The present work illustrates the power of compound 2 as a chiral, nonracemic, and stable 2-piperideine (enamine) equivalent in the rapid and efficient construction of 3-substituted piperidines (carbon−carbon and carbon−sulfur bonds) such as 3-spiropiperidines. This methodology offers a new route to such systems that could compete with previously reported strategies.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0499524