Enantiomers of nine arylglycine amides synthesized were successfully separated by capillary electrophoresis (CE) using highly sulfated beta-cyclodextrin (HS-beta-CD) as a chiral selector. Baseline enantioseparation of the analytes was obtained within 6 min at neutral pH but not the commonly used acidic condition. HS-beta-CD content, buffer type and concentration, and non-chiral additive were studied and optimized for high resolution and fast speed. A reproducible running buffer system composed of 15 g/L HS-beta-CD, 0 or 10% (volume fraction) methanol and 20 mmol/L 3-(N-morpholino) propane sulfonic acid at pH 6.5 was obtained. The D-enantiomer always migrated ahead of the L-enantiomer for all the 9 pairs of arylglycine amides. The migration order was found to be dependent on the structure of the solutes.
Download full-text PDF |
Source |
---|
Chem Commun (Camb)
December 2023
Jiangxi Province Key Laboratory of Synthetic Chemistry, School of Chemistry and Materials Science, East China University of Technology, Nanchang, 330013, China.
Organophotocatalytic cascade cross-dehydrogenative-coupling/cyclization reaction of -hydroxyarylenaminones with α-amino acid derivatives for the construction of α-chromone substituted α-amino acid derivatives was developed. Various -arylglycine esters, amides and dipeptides underwent the cascade cyclization reaction well with -hydroxyarylenaminones to afford the corresponding 3-aminoalkyl chromones in good to excellent yields. This approach consists of visible-light-promoted oxidation of α-amino acid derivatives, the Mannich reaction, and intramolecular nucleophilic cyclization under acidic conditions, and features a wide reaction scope, a simple operation and mild reaction conditions, which may have the potential to be used for the synthesis of bioactive molecules.
View Article and Find Full Text PDFOrg Lett
September 2018
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering , Southwest University, Chongqing 400715 , China.
Transformation of secondary amides to N-acylimines was used as an effective strategy to activate otherwise unreactive amide bonds. In this tandem reaction, the Rose Bengal-catalyzed photo-oxidative coupling of arylglycine esters and enamides generates N-acylimines, which undergo intramolecular transamidation and imine hydrolysis to afford bioactive acyl Mannich base derivatives under metal-free and mild conditions.
View Article and Find Full Text PDFJ Org Chem
September 2017
College of Chemistry & Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China.
In the presence of catalytic triarylamine radical cation, an sp-sp consecutive C-H functionalization of N-arylglycine amides was achieved, providing a series of isatin derivatives in high yields. In this transformation, the initial aerobic oxidation of the relatively active sp C-H bonds triggered the following intramolecular cyclization, in which the aniline group was employed as a removable auxiliary group to enable the consecutive process.
View Article and Find Full Text PDFOrg Lett
August 2016
Department of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt am Main, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany.
A general Pd-catalyzed, enantioselective three-component synthesis of α-arylglycines starting from sulfonamides, glyoxylic acid derivatives, and boronic acids was developed. This operationally straightforward procedure enables the preparation of a wide variety of α-arylglycines in high yields and excellent levels of enantioselectivity from a simple set of readily available starting materials. Incorporation of Pbf-amides gives a racemization-free access to N-unprotected α-arylglycines.
View Article and Find Full Text PDFJ Org Chem
February 2016
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8170, United States.
A high yielding and practical two-step synthesis of enantiomerically pure perfluorobutanesulfinamide from Senanayake's 2-aminoindanol-derived sulfinyl transfer reagent was developed and carried out on a multigram scale. Straightforward condensation of this sulfinamide with ethyl glyoxylate provided the N-perfluorobutanesulfinyl imino ester. The utility of this activated N-sulfinyl imino ester was demonstrated for reactions that gave either no product or very low yields with the corresponding less electrophilic N-tert-butanesulfinyl derivative.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!