The Enantioselective Dakin-West Reaction

Angewandte Chemie
Raffael C WendePeter R Schreiner

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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Citations

Jul 15, 2016·ACS Central Science·Yoann CotelleStefan Matile
Jun 8, 2017·Organic & Biomolecular Chemistry·Tobias SchnitzerHelma Wennemers
Mar 1, 2017·Chemical Communications : Chem Comm·My Linh TongStefan F Kirsch
Nov 7, 2017·Angewandte Chemie·Stefan Grimme, Peter R Schreiner
Apr 23, 2016·Chemical Communications : Chem Comm·Yongjin KimJaiwook Park
Jan 25, 2019·ChemMedChem·Janis MüllerGerhard Klebe
Dec 7, 2018·Chemical & Pharmaceutical Bulletin·Ko MorishitaHiroaki Shirahase
Jul 7, 2018·Beilstein Journal of Organic Chemistry·Andreas H HeindlHermann A Wegner
Apr 7, 2018·Science·Rupert S J ProctorRobert J Phipps
Dec 17, 2020·Organic & Biomolecular Chemistry·Lewis A T AllenPhilip J Parsons
Feb 23, 2021·The Journal of Organic Chemistry·Alexander SeitzPeter R Schreiner
Aug 15, 2018·Journal of the American Chemical Society·Carla RiglingHelma Wennemers
Oct 19, 2017·Journal of the American Chemical Society·Tobias Schnitzer, Helma Wennemers
Nov 26, 2019·The Journal of Organic Chemistry·Dominik NiedekPeter R Schreiner
Nov 12, 2021·The Journal of Organic Chemistry·Finn M WilmingPeter R Schreiner

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