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

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 produ...

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Bibliographic Details
Published in:Tetrahedron 2015-04, Vol.71 (17), p.2561-2571
Main Authors: Chrostowska, Anna, Darrigan, Clovis, Khayar, Said, Baylère, Patrick, Lewkowski, Jarosław, Krzyczmonik, Anna, Tokarz, Paweł, Ślepokura, Katarzyna, Lis, Tadeusz
Format: Article
Language:English
Subjects:
Chemical Sciences
Diamino-phosphonates with DACH moiety
Diastereoselective addition of phosphite
Inorganic chemistry
Ionization energies
or physical chemistry
Quantum calculations
Theoretical and
UV-photoelectron spectroscopy
X-ray structural study
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.03.010