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Title
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Hydride-promoted ring expansion of 2-azaspiropyrrolinium salts : an approach towards the synthesis of (-)-nitramine
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Author
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Abstract
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| 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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Language
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English
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Source (journal)
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Synlett : accounts and rapid communications in synthetic organic chemistry. - Stuttgart, 1989, currens
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Publication
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Stuttgart
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2005
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ISSN
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0936-5214
[print]
1437-2096
[online]
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DOI
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10.1055/S-2005-871555
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Volume/pages
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11
(2005)
, p. 1726-1730
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ISI
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000230448500017
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Full text (Publisher's DOI)
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