Periasamy, Mariappan ; Satish Kumar, Sakilam ; Sampath Kumar, N. (2008) Catalytic asymmetric dihydroxylation of substituted trans-stilbene derivatives: implications of the variation of enantioselectivities on the mechanism of OsO4 addition to olefins Tetrahedron Letters, 49 (28). 4416-4419 . ISSN 0040-4039
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2008.05.016
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Sharpless AD Reaction; 9-O-Acetyldihydrocinchonidine; trans-Stilbene; [3+2] Mechanism; Hammett Correlation |
| ID Code: | 37164 |
| Deposited On: | 25 Apr 2011 08:10 |
| Last Modified: | 25 Apr 2011 08:10 |
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