Enantioselective Rhodium-Catalysed Insertion of Trifluorodiazoethanes into Tin Hydrides

Tetrahedron 2019
S. Hyde, Jānis Veliks, D.M.H. Ascough, R. Szpera, R.S. Paton, V. Gouverneur

Aryl substituted 2,2,2-trifluorodiazoethanes undergo rhodium(II)-catalysed insertion reactions with tin hydrides affording the corresponding α-(trifluoromethyl)benzyl stannanes. This reactivity contrasts with that of diazo esters which predominantly afford CH2 reduction products in the presence of tin hydrides. The first example of asymmetric insertion into tin hydrides using diazo compounds is also described. In addition, this system extends to asymmetric germanium hydride and silane insertion.

Keywords
Asymmetric insertion, Germanium hydride, Silane, Stannane, Trifluorodiazoethane
DOI
10.1016/j.tet.2018.11.022
Hyperlink
https://www.sciencedirect.com/science/article/pii/S0040402018313620

Hyde, S., Veliks, J., Ascough, D., Szpera, R., Paton, R., Gouverneur, V. Enantioselective Rhodium-Catalysed Insertion of Trifluorodiazoethanes into Tin Hydrides. Tetrahedron, 2019, Vol. 75, No. 1, pp.17-25. ISSN 0040-4020. Available from: doi:10.1016/j.tet.2018.11.022

Publication language
English (en)