Journalartikel

Jahr der Veröffentlichung: 2016

Seiten: 2769-2773

Zeitschrift: Angewandte Chemie

Bandnummer: 128

Heftnummer: 8

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

Verlag: 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-Zitierstil: Wende, R., Seitz, A., Niedek, D., Schuler, S., Hofmann, C., Becker, J., et al. (2016) The Enantioselective Dakin–West Reaction, Angewandte Chemie, 128(8), pp. 2769-2773. https://doi.org/10.1002/ange.201509863

APA-Zitierstil: Wende, R., Seitz, A., Niedek, D., Schuler, S., Hofmann, C., Becker, J., & Schreiner, P. (2016). The Enantioselective Dakin–West Reaction. Angewandte Chemie. 128(8), 2769-2773. https://doi.org/10.1002/ange.201509863