Jump to main content
Jump to site search

Issue 11, 2014
Previous Article Next Article

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

Author affiliations

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.

Back to tab navigation

Supplementary files

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
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements