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  Home > JCE Print > Journal of Chemical Education > Issues > 2005  > January  >
In the Laboratory
The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory
Christopher J. Nichols and Melissa R. Taylor
Department of Chemistry, California State University, Chico, Chico, CA 95929-0210
Cover
January 2005
Vol. 82 No. 1
p. 105
Abstract
A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column.
Supplement
Instructions for the students, notes for the instructor, and NMR spectra of the alkene products and homemade DHQD esters are available.
*  Contents
*  Download
JCE2005p0105W.pdf
More Information
*  Citation
 Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ. 2005 82 105.
*  Keywords
 Chirality / Optical Isomers; Chromatography; IR Spectroscopy; Laboratory Instruction; NMR Spectrometry; Organic Chemistry; Organic Synthesis
*  History
 Created:
Last Updated:		 November 29, 2004
December 16, 2004
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