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Título

Symmetry Breaking of Novel C2 Chiral Across-Ring 1,3-Dienes

AutorNoheda Marín, Pedro ; García-Ruiz, Germán; Pozuelo, María C.; Abbassi, Khalid; Pascual-Alfonso, Eva; Alonso, José M. ; Jiménez-Barbero, Jesús
Fecha de publicación5-sep-1998
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 63(20): 6772–6773 (1998)
ResumenEnantiomerically pure C2-symmetric compounds are powerful tools for chemistry. Nevertheless, their use as chiral templates for the synthesis of unsymmetrical targets is only efficient provided that no additional elements or steps are required to improve the statistical results of the symmetry-breaking step. Monofunctionalization has been the unique strategy described for C2 symmetry breaking. Up to now, the possibility of a C2 symmetry breaking induced by a symmetry-driven functionalization at both homotopic sites remains experimentally unexplored.
We herein report on this possibility by using the formation of the unsymmetrical structures II as model.
Descripción2 pages, 4 schemes.-- Supporting Information Available: Experimental procedures and spectral data for compounds 3, meso-3, 6 and 9-18. Molecular mechanics protocol and discussion. Table 1 showing the steric energy values for the conformers of 10 and 12. Figures with a view of the most stable conformers (15 pages). Available at: http://pubs.acs.org/doi/suppl/10.1021/jo981296i/suppl_file/jo981296i_s.pdf
Versión del editorhttp://dx.doi.org/10.1021/jo981296i
URIhttp://hdl.handle.net/10261/11364
DOI10.1021/jo981296i
ISSN0022-3263
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