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

Authors:Noheda Marín, Pedro
García-Ruiz, Germán
Pozuelo, María C.
Abbassi, Khalid
Pascual-Alfonso, Eva
Alonso, José M.
Jiménez-Barbero, Jesús
Issue Date:5-Sep-1998
Publisher:American Chemical Society
Citation:Journal of Organic Chemistry 63(20): 6772–6773 (1998)
Abstract:Enantiomerically 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.
Description:2 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
Publisher version (URL):http://dx.doi.org/10.1021/jo981296i
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