The Enantioselective Dakin-West Reaction
Raffael C Wende1, Alexander Seitz1, Dominik Niedek1
1Institute of Organic Chemistry, Justus-Liebig University, 35392, Giessen, Germany.
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.
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