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DOI: 10.1039/A704413E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 3501-3508

Improved procedure for Juliá–Colonna asymmetric epoxidation of α,β-unsaturated ketones: total synthesis of diltiazem and Taxol[hair space]TM side-chain

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Brian M. Adger, James V. Barkley, Sophie Bergeron, Michael W. Cappi, Benjamin E. Flowerdew, Mark P. Jackson, Ray McCague, Thomas C. Nugent and Stanley M. Roberts

Abstract

Poly-L-leucine catalyses the asymmetric epoxidation of enones 1–6 efficiently in a non-aqueous medium to provide the epoxy ketones 7–12 (70–91% yield; 80 to [greater than or equal, slant]95% ee). The strategy was used to make diltiazem 16 and the Taxol[hair space]TM side chain 23 in single enantiomer form.

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