Novel Formal [3+3] Cycloaddition of Silyl Nitronates with Activated Cyclo­propanes and Its Application in the Synthesis of Pyrroline-N-oxides

Abstract 1,1-Cyclopropane diesters with donor substituents undergo formal [3+3] cycloaddition with various silyl nitronates under Yb(OTf) 3 catalysis in the presence of a proton scavenger to give target N -silyloxy tetrahydro-1,2-oxazines in 56–98% yield. The reasons determining the reaction diaster...

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Bibliographic Details
Published in:Synlett 2014-10, Vol.25 (16), p.2275-2280
Main Authors: Mikhaylov, Andrey A., Novikov, Roman A., Khomutova, Yulia A., Arkhipov, Dmitry E., Korlyukov, Alexander A., Tabolin, Andrey A., Tomilov, Yury V., Ioffe, Sema L.
Format: Article
Language:English
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cluster
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Summary:Abstract 1,1-Cyclopropane diesters with donor substituents undergo formal [3+3] cycloaddition with various silyl nitronates under Yb(OTf) 3 catalysis in the presence of a proton scavenger to give target N -silyloxy tetrahydro-1,2-oxazines in 56–98% yield. The reasons determining the reaction diastereoselectivity are discussed. The resulting tetrahydro-1,2-oxazines are transformed into pyrroline- N -oxides via a novel TfOH-promoted silanol elimination reaction.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1378564