Journal article

Publication year: 2016

Pages: 2719-2723

Journal: Angewandte Chemie International Edition

Volume number: 55

Issue number: 8

DOI Link: https://doi.org/10.1002/anie.201509863

Publisher: Wiley

Abstract: 

Here we report the development of the first enantioselective Dakin–West
reaction, yielding α‐acetamido methylketones with up to 58 % ee with good yields. Two of the obtained products were recrystallized once to achieve up to 84 % ee.
The employed methylimidazole‐containing oligopeptides catalyze both the
acetylation of the azlactone intermediate and the terminal
enantioselective decarboxylative protonation. We propose a
dispersion‐controlled reaction path that determines the asymmetric
reprotonation of the intermediate enolate after the decarboxylation.

Harvard Citation style: Wende, R., Seitz, A., Niedek, D., Schuler, S., Hofmann, C., Becker, J., et al. (2016) The Enantioselective Dakin–West Reaction, Angewandte Chemie International Edition, 55(8), pp. 2719-2723. https://doi.org/10.1002/anie.201509863

APA Citation style: Wende, R., Seitz, A., Niedek, D., Schuler, S., Hofmann, C., Becker, J., & Schreiner, P. (2016). The Enantioselective Dakin–West Reaction. Angewandte Chemie International Edition. 55(8), 2719-2723. https://doi.org/10.1002/anie.201509863