Journal article

Publication year: 2013

Pages: 8465-8484

Journal: The Journal of Organic Chemistry

Volume number: 78

Issue number: 17

DOI Link: https://doi.org/10.1021/jo401195c

Publisher: American Chemical Society

Abstract: 

Inspired by the extraordinary selectivities of acylases, we envisioned
the use of lipophilic oligopeptidic organocatalysts for the acylative
kinetic resolution/desymmetrization of rac- and meso-cycloalkane-1,2-diols.
Here we describe in a full account the discovery and development
process from the theoretical concept to the final catalyst, including
scope and limitations. Competition experiments with various alcohols and
electrophiles show the full potential of the employed oligopeptides.
Additionally, we utilized NMR and IR-spectroscopic methods as well as
computations to shed light on the factors responsible for the
selectivity. The catalyst system can be readily modified to a
multicatalyst by adding other catalytically active amino acids to the
peptide backbone, enabling the stereoselective one-pot synthesis of
complex molecules from simple starting materials

Harvard Citation style: Müller, C., Zell, D., Hrdina, R., Wende, R., Wanka, L., Schuler, S., et al. (2013) Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols, The Journal of Organic Chemistry, 78(17), pp. 8465-8484. https://doi.org/10.1021/jo401195c

APA Citation style: Müller, C., Zell, D., Hrdina, R., Wende, R., Wanka, L., Schuler, S., & Schreiner, P. (2013). Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols. The Journal of Organic Chemistry. 78(17), 8465-8484. https://doi.org/10.1021/jo401195c