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1999
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In the Laboratory
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Sharpless Asymmetric Dihydroxylation: Effect of Alkene Structure on Rates and Selectivity
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Alan C. Spivey, R. Hanson, N. Scorah, and S. J. Thorpe
University of Sheffield, Department of Chemistry, Sheffield S3 7HF, UNITED KINGDOM
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May 1999
Vol. 76 No. 5
p. 655
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| Abstract |
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This article describes a laboratory experiment for undergraduates to be performed by a group of six students. It involves the Sharpless asymmetric cis-dihydroxylation (AD) of a series of alkenes. Each student is assigned an alkene and performs three dihydroxylation reactions: one racemic and two enantioselective variants. The products are characterized by 1H NMR, IR, MS, [a]D20, and chiral chromatography (HPLC or GC). Comparison by the students of their results with those reported in the literature, particularly the extensive work of Sharpless, allows an exploration of the validity of Sharpless's mnemonic for predicting the stereochemical outcome of these reactions. Analysis of the results of the whole group by each student provides a useful framework within which to explore and re-enforce many of the essential concepts of stereochemistry, catalysis, and process optimization of enantioselective catalytic procedures.
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| More Information |
 Citation |
Spivey, Alan C.; Hanson, R.; Scorah, N.; Thorpe, S. J. J. Chem. Educ. 1999 76 655.
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Keywords |
Laboratory Instruction; Organic Chemistry; Synthesis; Catalysis; Stereochemistry; Organometallics; Organic Synthesis
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History |
Created:
Last Updated: |
June 11, 1999
June 23, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
1999
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May
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655
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