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Synthesis 2011(15): 2415-2422  
DOI: 10.1055/s-0030-1260108
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Andrey A. Tabolin*a, Yulia A. Khomutovaa, Yulia V. Nelyubinab, Sema L. Ioffe*a, Vladimir A. Tartakovskya
a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russian Federation
Fax: +7(499)1355328; e-Mail: iof@ioc.ac.ru;
b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow 119991, Russian Federation
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Publication History

Received 4 April 2011
Publication Date:
14 July 2011 (online)

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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.

Key words

nitroso acetals - rearrangement - nitrogen heterocycles - 1,2-oxazines - aliphatic nitro compounds

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Crystallographic data for the structure 4a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 805539. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.