A comparative study on the allylation of a benzoyl hydrazone with allyl trichlorosilane using monosulfoxides, methylene-bridged C2-symmetric bissulfoxides, and ethylene-bridged C2-symmetric bissulfoxides shows that the enantioselectivity of the process is highly dependent on the spacer between the two sulfinyl sulfurs and the concentration of the reaction.
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http://dx.doi.org/10.1021/ol070729d | DOI Listing |
J Org Chem
July 2013
Instituto de Investigaciones Quı́micas, CSIC-Universidad de Sevilla, c/. Américo Vespucio, 49., Isla de la Cartuja, 41092 Sevilla, Spain.
The application of acyclic C2-symmetric chelating bis-sulfoxide ligands in the Rh(I)-catalyzed enantioselective 1,4-addition of boronic acids to electron-deficient alkenes is reported. Among the acyclic ethane-bridged bis-sulfoxides tested, the ligand Ferbisox (11), bearing ferrocenyl moieties as substituents at the sulfinyl sulfurs, has exhibited the best results in terms of chemical yield (up to 96%) and enantioselectivity (up to 97% ee). The conjugate addition takes place smoothly in toluene at room temperature in short reaction times (typically 2 h).
View Article and Find Full Text PDFOrg Lett
May 2007
Departamento de Química OrgAnica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla, 41012 Sevilla, Spain.
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