Skip to Main content Skip to Navigation
Journal articles

Diastereoselective synthesis of tetraalkyl (R,R)-1,2-cyclohexylene-diamino-di-phosphonates bearing thiophene, furan and pyrrole moieties. Computational and experimental study on their formation

Abstract : Diastereoselective additions of dialkyl phosphites to three diimines bearing DACH moiety and thiophene, furan or pyrrole rings were studied in the aspect of their stereochemistry, structure of predominant products and mechanism. For these reasons, analysis of reaction mixture, X-ray studies of products, UV-photoelectron spectroscopy and ionization energies of the starting imines were performed experimentally while reaction profiles were calculated at the CAM-B3LYP/6-311G(d,p) level of theory. The calculated energy barriers corresponding to the gas phase are significantly low and seem to explain why the products are formed relatively easily.
Complete list of metadata

https://hal.archives-ouvertes.fr/hal-01549704
Contributor : Sylvie Blanc <>
Submitted on : Thursday, June 29, 2017 - 9:45:52 AM
Last modification on : Tuesday, February 2, 2021 - 2:58:05 PM

Identifiers

Collections

Citation

Anna Chrostowska, Clovis Darrigan, S. Khayar, Patrick Baylère, J. Lewkowski, et al.. Diastereoselective synthesis of tetraalkyl (R,R)-1,2-cyclohexylene-diamino-di-phosphonates bearing thiophene, furan and pyrrole moieties. Computational and experimental study on their formation. Tetrahedron, Elsevier, 2015, 71 (17), pp.2561-2571. ⟨10.1016/j.tet.2015.03.010⟩. ⟨hal-01549704⟩

Share

Metrics

Record views

129