Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: one-pot three-component assembly of fluorinated bicyclic nitroso acetals

Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: one-pot three-component assembly of fluorinated bicyclic nitroso acetals Full article

Journal

Organic Chemistry Frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129

Output data

Year: 2018, Volume: 5, Number: 17, Pages: 2588-2594 Pages count : 7 DOI: 10.1039/c8qo00623g

Authors

Motornov Vladimir A. ^1,2 , Tabolin Andrey A. ¹ , Novikov Roman A. ^1,3 , Nelyubina Yulia V. ⁴ , Nenajdenko Valentine G. ⁵ , Ioffe Sema L. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, Russia
2	Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow 125047, Russia
3	V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, Moscow, Russia
4	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow, Russia
5	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia

A one-pot three-component route towards fluorinated five/five-annulated nitroso acetals bearing two fused isoxazolidine rings is described. Target nitroso acetals were obtained with complete regioselectivity and high stereoselectivity. The mechanism of this tandem [4 + 1]/[3 + 2] cycloaddition was proposed to include the intermediate formation of elusive 3-fluoro-isoxazoline-N-oxides as key intermediates. This method is applicable for the synthesis of a broad scope of nitroso acetals starting from various fluoronitroalkenes, halogenated dicarbonyl compounds and dipolarophiles of different electronic nature.

Motornov V.A. , Tabolin A.A. , Novikov R.A. , Nelyubina Y.V. , Nenajdenko V.G. , Ioffe S.L.
Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: one-pot three-component assembly of fluorinated bicyclic nitroso acetals
Organic Chemistry Frontiers. 2018. V.5. N17. P.2588-2594. DOI: 10.1039/c8qo00623g WOS Scopus OpenAlex

≡ Web of science:	WOS:000443281400012
≡ Scopus:	2-s2.0-85051996067
≡ OpenAlex:	W2887098499