title: The Enantioselective Dakin-West Reaction.
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.
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University, 35392, Giessen, Germany.
authors.forename: Raffael C
authors.initials: RC
authors.lastname: Wende
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University, 35392, Giessen, Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Seitz
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University, 35392, Giessen, Germany.
authors.forename: Dominik
authors.initials: D
authors.lastname: Niedek
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University, 35392, Giessen, Germany.
authors.forename: Sören M M
authors.initials: SM
authors.lastname: Schuler
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University, 35392, Giessen, Germany.
authors.forename: Christine
authors.initials: C
authors.lastname: Hofmann
authors.affiliation: Institute of Inorganic and Analytical Chemistry, Justus-Liebig University, 35392, Giessen, Germany.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Becker
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University, 35392, Giessen, Germany. prs@uni-giessen.de.
authors.forename: Peter R
authors.identifier: http://orcid.org/0000-0002-3608-5515
authors.initials: PR
authors.lastname: Schreiner
keywords: amino acids; noncovalent interactions; organocatalysis; peptides; protonation