Title
Hydride-promoted ring expansion of 2-azaspiropyrrolinium salts : an approach towards the synthesis of (-)-nitramineHydride-promoted ring expansion of 2-azaspiropyrrolinium salts : an approach towards the synthesis of (-)-nitramine
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Stuttgart,
Subject
Chemistry
Source (journal)
Synlett: accounts and rapid communications in synthetic organic chemistry. - Stuttgart
Volume/pages
(2005):11, p. 1726-1730
ISSN
0936-5214
ISI
000230448500017
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Abstract
An enantioselective approach toward the synthesis of the spiroalkaloid (-)-nitramine was achieved by electrophile-induced cyclization of a suitably substituted and protected chiral alpha-allylcyc lohexanecarboxaldi mine. 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.
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