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The Enantioselective Dakin–West Reaction
Author(s) -
Wende Raffael C.,
Seitz Alexander,
Niedek Dominik,
Schuler Sören M. M.,
Hofmann Christine,
Becker Jonathan,
Schreiner Peter R.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509863
Subject(s) - enantioselective synthesis , protonation , chemistry , decarboxylation , acetylation , stereochemistry , organic chemistry , catalysis , biochemistry , ion , gene
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.