New Rearrangement of Conjugated Cyclic Ene Nitroso O-Trimethylsilyl Acetals: Convenient Synthesis of Dihydro-2H-pyran-3-one and Dihydrofuran-3-one Oximes

Abstract The nucleophile-induced rearrangement of cyclic N-alkoxy-N-(silyloxy)enamines was investigated. As a result, a new strategy for the synthesis of β-pyranone and β-furanone derivatives from nitro compounds is suggested.

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2011-08, Vol.2011 (15), p.2415-2422
Main Authors: Tabolin, Andrey A., Khomutova, Yulia A., Nelyubina, Yulia V., Ioffe, Sema L., Tartakovsky, Vladimir A.
Format: Article
Language:English
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Description
Summary:Abstract The nucleophile-induced rearrangement of cyclic N-alkoxy-N-(silyloxy)enamines was investigated. As a result, a new strategy for the synthesis of β-pyranone and β-furanone derivatives from nitro compounds is suggested.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1260108