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_aSpivey, Alan C.
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_aSharpless asymmetric dihydroxylation.
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_aunmediated
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_avolume
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_aABSTRACT : 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.
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648 _2
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_xExperiments.
_aChemistry;Alkenes.;Chemical structure.
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_aHanson, R.;Scorah, N.
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_g 76 (5) : May 1999. pp. 655-659.
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_tJournal of Chemical Education
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