4.5 Article

A New Sequential Intramolecular Cyclization Based on the Boekelheide Rearrangement

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 2, Pages 271-279

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000936

Keywords

Pyridine N-oxides; Boekelheide rearrangement; Cyclization; Intramolecular reactions; Nitrogen heterocycles; Synthetic methods

Funding

  1. GlaxoSmithKline of Verona

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Pyrrolidines and piperidines were synthesized from (aminoalkyl)pyridine N-oxides with a general and quite efficient method developed by using di-tert-butylsilyl bis(trifluoromethanesulfonate) as a new promoter for a Boekelheide-type reaction. The use of a new Boekelheide promoter, which is compatible with amino groups, opens new perspectives in view of its application in intramolecular cyclizations.

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