Adelaide Research & Scholarship
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https://hdl.handle.net/2440/4871
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| Type: | Journal article |
| Title: | An investigative study of kinetic resolutions by the Sharpless asymmetric dihydroxylation reaction |
| Author: | Hamon, David P. G. Tuck, Kellie Louise Christie, Hamish Saul |
| Citation: | Tetrahedron, 2001; 57(46):9499-9508 |
| Publisher: | Pergamon-Elsevier Science Limited |
| Issue Date: | 2001 |
| ISSN: | 0040-4020 |
| School/Discipline: | School of Chemistry and Physics : Chemistry |
| Statement of Responsibility: | David P.G Hamon, Kellie L Tuck and Hamish S Christie |
| Abstract: | The requirements for a highly selective kinetic resolution with the Sharpless asymmetric dihydroxylation (AD) reaction were investigated with a number of alkene substrates. It was found that with 1-phenyl-4-tert-butylcyclohexene enantioselectivity is very high, yet diastereoselectivity is poor and kinetic resolution is ineffective. With 5-methyl-2-phenylbicyclo[3.2.0]heptan-2-ene both diastereoselectivity and enantioselectivity are high and kinetic resolution is effective. It was discovered that the transition state for the product-determining step in the Sharpless AD reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered. It was discovered that the transition state for the product-determining step in the Sharpless asymmetric dihydroxylation reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered. |
| Keywords: | sharpless asymmetric dihydroxylation ; kinetic resolutions ; transition state |
| Description: | Available online 5 November 2001. |
| Rights: | Copyright © 2001 Elsevier Science Ltd. All rights reserved. |
| DOI: | 10.1016/S0040-4020(01)00948-6 |
| Appears in Collections: | Chemistry publications |
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