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Oxazolidinone cross-alkylation during Evans' asymmetric alkylation reaction

Author:
Fresno López, Nieves; Pérez Fernández, Ruth; Goya Laza, Pilar; Jimeno Herránz, María Luisa; Alkorta Osoro, Ibón; Elguero Bertolini, José; Menéndez Taboada, LauraUniovi authority; García-Granda, SantiagoUniovi authority
Subject:

Oxazolidinone; Asymmetric Alkylation; X-Ray Crystallography; Multinuclear Nmr; Dft Calculations

Publication date:
2011
Publisher version:
http://dx.doi.org/10.1016/j.tet.2011.09.083
Citación:
Tetrahedron, 67(47), P. 9104-9111 (2011); doi:10.1016/j.tet.2011.09.083
Abstract:

Starting from Evans’ imidazolidin-2-one (1) two compounds were obtained by trans-N-acylation: the expected one 3 with S,R configuration and a second compound 5, that is, related to 3 by the loss of a CH(CH3)Cdouble bond; length as m-dashO fragment. The stereochemistry of 3 was established by NMR spectroscopy, mainly NOE experiments, as expected, the new center has an S configuration, the compound being thus S,R. The structure of compound 5 was determined by X-ray crystallography. A mechanism of formation of 5 was proposed.

Starting from Evans’ imidazolidin-2-one (1) two compounds were obtained by trans-N-acylation: the expected one 3 with S,R configuration and a second compound 5, that is, related to 3 by the loss of a CH(CH3)Cdouble bond; length as m-dashO fragment. The stereochemistry of 3 was established by NMR spectroscopy, mainly NOE experiments, as expected, the new center has an S configuration, the compound being thus S,R. The structure of compound 5 was determined by X-ray crystallography. A mechanism of formation of 5 was proposed.

URI:
http://hdl.handle.net/10651/10670
ISSN:
0040-4020
Identificador local:

20111285

DOI:
10.1016/j.tet.2011.09.083
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