5469-44-3Relevant articles and documents
The Enantioselective Dakin-West Reaction
Wende, Raffael C.,Seitz, Alexander,Niedek, Dominik,Schuler, S?ren M. M.,Hofmann, Christine,Becker, Jonathan,Schreiner, Peter R.
supporting information, p. 2719 - 2723 (2016/02/27)
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.
Diastereochemical diversity of imidazoline scaffolds via substrate controlled TMSCI mediated cycloaddition of azlactones
Sharma, Vasudha,Tepe, Jetze J.
, p. 5091 - 5094 (2007/10/03)
(Chemical Equation Presented) We report herein a trimethylsilyl chloride mediated substrate controlled 1,3-dipolar cycloaddition for the diastereoselective synthesis of either syn- or anti-imidazolines. This method provides scaffolds with four points of diversity and control over two stereocenters.
ASYMMETRIC SYNTHESIS OF AMINO ACIDS VIA THE CATALYTIC REDUCTION OF SUBSTITUTED ACYLAMINOACRYLIC ACID AZLACTONE DERIVATIVES. 25. REDUCTIVE AMINOLYSIS OF 2-PHENYL- AND 2-METHYL-Δ2-OXAZOLIN-5-ONES UPON TREATMENT WITH A CHIRAL PdCl2-R-PHENYLGLYCINE
Chel'tsova, G. V.,Karpeiskaya, E. I.,Klabunovskii, E. I.
, p. 727 - 731 (2007/10/02)
We have studied the reaction of Δ2-oxazolin-5-ones with R-phenylglycine methyl ester in the presence of PdCl2; the reaction gives phenylalanine or valine dipeptide derivatives with the RS-configuration.The presence of triethylamine during the r