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

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

Journal

Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096

Output data

Year: 2014, Volume: 25, Number: 16, Pages: 2275-2280 Pages count : 6 DOI: 10.1055/s-0034-1378564

Authors

Mikhaylov Andrey A. ¹ , Novikov Roman A. ¹ , Khomutova Yulia A. ¹ , Arkhipov Dmitry E. ² , Korlyukov Alexander A. ² , Tabolin Andrey A. ¹ , Tomilov Yury V. ¹ , Ioffe Sema L. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
2	A. N. Nesmeyanov Institute of Organoelement Compounds

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.

Mikhaylov A.A. , Novikov R.A. , Khomutova Y.A. , Arkhipov D.E. , Korlyukov A.A. , Tabolin A.A. , Tomilov Y.V. , Ioffe S.L.
Novel Formal [3+3] Cycloaddition of Silyl Nitronates with Activated Cyclopropanes and Its Application in the Synthesis of Pyrroline-N-oxides
Synlett. 2014. V.25. N16. P.2275-2280. DOI: 10.1055/s-0034-1378564 WOS OpenAlex

≡ Web of science:	WOS:000342570400012
≡ OpenAlex:	W2314163828

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

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