The Enantioselective Dakin–West Reaction. (25th January 2016)

• Record Type: Journal Article
• Authors: Wende, Raffael C.; Seitz, Alexander; Niedek, Dominik; Schuler, Sören M. M.; Hofmann, Christine; Becker, Jonathan; Schreiner, Peter R.
• Is Part Of: Angewandte Chemie. Volume 128:Number 8(2016)
• Page Start: 2769
• Page End: 2773
• Publication Date: 2016-01-25
• Subjects: Aminosäuren -- Nichtkovalente Wechselwirkungen -- Organokatalyse -- Peptide -- Protonierung; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201509863
• Languages: English
• ISSNs: 0044-8249

Abstract

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.