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Science 15 August 1997:
Vol. 277. no. 5328, pp. 936 - 938
DOI: 10.1126/science.277.5328.936
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Reports

Asymmetric Catalysis with Water: Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic Hydrolysis

Makoto Tokunaga, Jay F. Larrow, Fumitoshi Kakiuchi, Eric N. Jacobsen

Epoxides are versatile building blocks for organic synthesis. However, terminal epoxides are arguably the most important subclass of these compounds, and no general and practical method exists for their production in enantiomerically pure form. Terminal epoxides are available very inexpensively as racemic mixtures, and kinetic resolution is an attractive strategy for the production of optically active epoxides, given an economical and operationally simple method. Readily accessible synthetic catalysts (chiral cobalt-based salen complexes) have been used for the efficient asymmetric hydrolysis of terminal epoxides. This process uses water as the only reagent, no added solvent, and low loadings of a recyclable catalyst (<0.5 mole percent), and it affords highly valuable terminal epoxides and 1,2-diols in high yield with high enantiomeric enrichment.

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.

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THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Epoxide-Opening Cascades Promoted by Water.
I. Vilotijevic and T. F. Jamison (2007)
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Asymmetric Catalysis Special Feature Part II: Highly enantioselective epoxidation of styrenes: Implication of an electronic effect on the competition between spiro and planar transition states.
M. Hickey, D. Goeddel, Z. Crane, and Y. Shi (2004)
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Asymmetric Catalysis Special Feature Part I: Asymmetric hetero-Diels-Alder reaction catalyzed by dirhodium(II) carboxamidates.
M. P. Doyle, M. Valenzuela, and P. Huang (2004)
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Asymmetric Catalysis Special Feature Part I: An efficient, palladium-catalyzed, enantioselective synthesis of (2R)-3-butene-1,2-diol and its use in highly selective Heck reactions.
N. Cheeseman, M. Fox, M. Jackson, I. C. Lennon, and G. Meek (2004)
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Privileged Chiral Catalysts.
T. P. Yoon and E. N. Jacobsen (2003)
Science 299, 1691-1693
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