Tandem [3+2]-cycloaddition/homo-Baldwin rearrangement of silyl nitronates and donor-acceptor cyclopropenes. A novel approach to polysubstituted aziridines starting from nitro compounds

Tandem [3+2]-cycloaddition/homo-Baldwin rearrangement of silyl nitronates and donor-acceptor cyclopropenes. A novel approach to polysubstituted aziridines starting from nitro compounds Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2022, Volume: 110, Article number : 132693, Pages count : DOI: 10.1016/j.tet.2022.132693

Authors

Lichtenstein Yana I. ¹ , Golovanov Ivan S. ¹ , Ioffe Sema L. ¹ , Tabolin Andrey A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, Moscow, 119991, Russia

The synthesis of substituted N-silyloxy aziridines through reaction of silyl nitronates and enol diazo acetates is described. The process involves in situ transformation of enol diazo acetates into donor-acceptor cyclopropenes, their [3 + 2]-cycloaddition with nitronates and subsequent rearrangement of fused isoxazolidine intermediates. Depending on the substrate type, generation of prerequisite cyclopropenes could be promoted by various rhodium carboxylates (acetate, octanoate) in catalysts loadings as low as 50 ppm. Relative configuration of all three stereocenters in aziridine ring was established by NMR techniques and supported by quantum chemical calculations.

Lichtenstein Y.I. , Golovanov I.S. , Ioffe S.L. , Tabolin A.A.
Tandem [3+2]-cycloaddition/homo-Baldwin rearrangement of silyl nitronates and donor-acceptor cyclopropenes. A novel approach to polysubstituted aziridines starting from nitro compounds
Tetrahedron. 2022. V.110. 132693 . DOI: 10.1016/j.tet.2022.132693 WOS Scopus OpenAlex

≡ Web of science:	WOS:000777863500010
≡ Scopus:	2-s2.0-85125323683
≡ OpenAlex:	W4213032142