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

Autor:	Sema L. Ioffe, Alexander A. Korlyukov, Yury V. Tomilov, Dmitry E. Arkhipov, Roman A. Novikov, Andrey A. Mikhaylov, Yulia A. Khomutova, Andrey A. Tabolin
Rok vydání:	2014
Předmět:	chemistry.chemical_compound Silanol Elimination reaction Silylation chemistry Yield (chemistry) Organic Chemistry Organic chemistry Pyrroline Medicinal chemistry Cycloaddition Scavenger (chemistry) Catalysis
Zdroj:	Synlett. 25:2275-2280
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0034-1378564
Popis:	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.
Databáze:	OpenAIRE
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