Hydride-Promoted Ring Expansion of 2-Azaspiropyrrolinium Salts: An Approach Towards the Synthesis of (-)-Nitramine

Abstract An enantioselective approach toward the synthesis of the spiroalkaloid (-)-nitramine was achieved by electrophile-induced cyclization of a suitably substituted and protected chiral α-allylcyclohexanecarboxaldimine. Its hydride-promoted ring expansion after spirocyclization gave rise to the...

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Bibliographic Details
Published in:Synlett 2005-07, Vol.2005 (11), p.1726-1730
Main Authors: Rosas Alonso, Erick, Tehrani, Kourosch Abbaspour, Boelens, Mark, De Kimpe, Norbert
Format: Article
Language:English
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Summary:Abstract An enantioselective approach toward the synthesis of the spiroalkaloid (-)-nitramine was achieved by electrophile-induced cyclization of a suitably substituted and protected chiral α-allylcyclohexanecarboxaldimine. Its hydride-promoted ring expansion after spirocyclization gave rise to the competitive formation of isomeric spiropyrrolidines and a spiropiperidine, the latter being further transformed into (-)-nitramine.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2005-871555