Catalytic asymmetric dihydroxylation of substituted trans-stilbene derivatives: implications of the variation of enantioselectivities on the mechanism of OsO4 addition to olefins |
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Authors: | Mariappan Periasamy Sakilam Satish Kumar N Sampath Kumar |
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Institution: | School of Chemistry, University of Hyderabad, Central University P.O., Hyderabad 500 046, India |
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Abstract: | The OsO4 catalyzed asymmetric dihydroxylation of substituted trans-stilbene derivatives using 9-O-acetyldihydrocinchonidine as chiral ligand gives the corresponding diols with lower enantioselectivity in the case of substrates containing electron-donating and electron-withdrawing substituents. The Hammett correlations of the enantiomeric ratios exhibit non-linear plots, in accordance with the conclusion that the reaction involves a 1,3-dipolar type 3+2] cycloaddition transition state. |
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Keywords: | Sharpless AD reaction 9-O-Acetyldihydrocinchonidine trans-Stilbene [3+2] Mechanism Hammett correlation |
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