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Issue 11, 2014
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Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation.

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Abstract

We detail an investigation of a peptide-based catalyst (6) that is effective for the site- (>100 : 1 : 1) and enantioselective epoxidation (86% ee) of farnesol. Studies of the substrate scope exhibited by the catalyst are included, along with an exploration of optimized reaction conditions. Mechanistic studies are reported, including relative rate determinations for the catalyst and propionic acid, a historical perspective, truncation studies, and modeling using NMR data. Our compiled data advances our understanding of the inner workings of a catalyst that was identified through combinatorial means.

Graphical abstract: Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation.

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Publication details

The article was received on 16 May 2014, accepted on 26 Jun 2014 and first published on 11 Aug 2014


Article type: Edge Article
DOI: 10.1039/C4SC01440E
Citation: Chem. Sci., 2014,5, 4504-4511
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    Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation.

    N. C. Abascal, P. A. Lichtor, M. W. Giuliano and S. J. Miller, Chem. Sci., 2014, 5, 4504
    DOI: 10.1039/C4SC01440E

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