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Asymmetric Epoxidation Catalyzed by α,α-Dimethylmorpholinone Ketone. Methyl Group Effect on Spiro and Planar Transition States

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Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523
[email protected]
Cite this: J. Org. Chem. 2009, 74, 16, 6335–6338
Publication Date (Web):July 16, 2009
https://doi.org/10.1021/jo900739q
Copyright © 2009 American Chemical Society
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Abstract

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Asymmetric epoxidation of olefins by using an α,α-dimethylmorpholinone-containing chiral ketone catalyst (4) has been investigated. This ketone, which has the combined features of several previously studied catalysts, is an effective catalyst for trans- and trisubstituted olefins, and up to 97% ee has been achieved. The α,α-dimethyl group has significant impact on spiro and planar transition states.

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The characterization of epoxides, the X-ray structure of ketone 4, the structure overlay of ketones 1 and 4, the NMR spectra of compound 6 and ketone 4, and the data for the determination of the enantiomeric excess of the epoxides obtained with ketone 4. This material is available free of charge via the Internet at http://pubs.acs.org.

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  30. O. Andrea Wong, Bin Wang, Mei-Xin Zhao, Yian Shi. ChemInform Abstract: Asymmetric Epoxidation Catalyzed by α,α-Dimethylmorpholinone Ketone. Methyl Group Effect on Spiro and Planar Transition States.. ChemInform 2010, 41 (2) https://doi.org/10.1002/chin.201002112
  31. Valeri V. Mossine, Thomas P. Mawhinney. 1-Amino-1-deoxy-d-fructose (“Fructosamine”) and its Derivatives. 2010,,, 291-402. https://doi.org/10.1016/S0065-2318(10)64006-1
  32. Simon E. Lewis. Synthetic methods : Part (ii) Oxidation and reduction methods. Annual Reports Section "B" (Organic Chemistry) 2010, 106 , 34. https://doi.org/10.1039/b927087f

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