An investigative study of kinetic resolutions by the Sharpless asymmetric dihydroxylation reaction
Date
2001
Authors
Hamon, David P. G.
Tuck, Kellie Louise
Christie, Hamish Saul
Editors
Advisors
Journal Title
Journal ISSN
Volume Title
Type:
Journal article
Citation
Tetrahedron, 2001; 57(46):9499-9508
Statement of Responsibility
David P.G Hamon, Kellie L Tuck and Hamish S Christie
Conference Name
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.
School/Discipline
School of Chemistry and Physics : Chemistry
Dissertation Note
Provenance
Description
Available online 5 November 2001.
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Copyright © 2001 Elsevier Science Ltd. All rights reserved.