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2000
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February
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In the Laboratory
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Catalytic Asymmetric Epoxidation Using a Fructose-Derived Catalyst
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Andy Burke, Patrick Dillon, Kyle Martin, and T. W. Hanks
Department of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, SC 29613-0420
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February 2000
Vol. 77 No. 2
p. 271
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| Abstract |
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Modern epoxidation methods are able to create two adjacent stereocenters with very high enantioselectivity. Opening of the epoxides with nucleophiles permits rapid entry into complex organic systems, making this powerful synthetic methodology one of the fundamental reactions in organic synthesis. Various reagents for generating epoxides have been developed, including the dioxiranes. These oxidants are typically generated in situ from a ketone. Recently, a chiral dioxirane has been prepared from fructose and shown to catalytically deliver an oxygen from a simple, symmetrical oxidant to a wide variety of alkenes in very high yields and with excellent selectivity. This reaction makes an effective experiment for advanced undergraduates. Both the synthesis of the catalyst and the epoxide product are easily purified and lend themselves well to analysis by the standard array of techniques available to the organic chemist. Enantioselectivity can be determined either by polarimetry or by NMR shift experiments. In addition, the mechanism of the asymmetric epoxidation can be explored by a combination of computer modeling and student-proposed research experiments.
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| Supplement |
Detailed handouts and instructions, instructor notes, and experimental data are provided.
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| More Information |
Citation |
Burke, Andy; Dillon, Patrick; Martin, Kyle; Hanks, Timothy W. J. Chem. Educ. 2000 77 271.
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Keywords |
Laboratory Instruction; Organic Chemistry; Catalysis; NMR Spectrometry; Stereochemistry; Organic Synthesis
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History |
Created:
Last Updated: |
January 5, 2000
August 31, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
2000
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February
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271
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