98%
921
2 minutes
20
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/chem.201000094 | DOI Listing |
Org Lett
September 2025
Departament de Química Orgànica, Facultat de Química, Universitat de València, C. Dr. Moliner 50, 46100 Burjassot, Spain.
Vinylogous isocyano esters were prepared for the first time. They react with aldehydes to give chiral oxazolines bearing a pendant conjugated ester under synergistic silver/organocatalysis. The reaction is carried out using a bifunctional squaramide in combination with silver oxide and performs well with a number of aryl, heteroaryl, and cycloalkyl aldehydes, providing the expected heterocycles in good yields with good diastereoselectivity and enantiomeric excesses ranging from 60% to 95% ee.
View Article and Find Full Text PDFJ Org Chem
August 2025
Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, China.
A highly enantioselective Michael reaction of benzofuran-derived azadienes with 3-fluorooxindoles, catalyzed by a quinine-derived squaramide catalyst, was developed. This protocol efficiently constructs a variety of 3-substituted-3-fluorooxindoles featuring two vicinal chirality centers, achieving good to high yields (68-92%) along with moderate to excellent enantioselectivities (70 to >99% ee) and diastereoselectivities (60:40 to >99:1 dr).
View Article and Find Full Text PDFNat Commun
July 2025
Institute of Drug Discovery and Design, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang, China.
Kinetic resolution is a promising strategy for accessing enantioenriched molecules from racemic mixtures. However, this method has not previously been realized in the synthesis of chiral sulfinyl scaffolds via S(IV)-X bond exchange. We disclose a kinetic resolution reaction of sulfinamides with alcohols in this report.
View Article and Find Full Text PDFChem Sci
July 2025
Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne 1015 Lausanne Switzerland
We report the diastereoselective and enantioselective synthesis of thio-substituted cyclobutanes a sulfa-Michael addition using cyclobutenes. In the presence of DBU, various thio-cyclobutane esters and amides were obtained in up to quantitative yield and >95 : 5 dr. Using a chiral chinchona-based squaramide bifunctional acid-base catalyst and an -acyl-oxazolidinone-substituted cyclobutene, thio-cyclobutanes were obtained with high yield and enantioselectivity (er up to 99.
View Article and Find Full Text PDFMolecules
April 2025
Key Laboratory of Medicinal Molecule Science and Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China.
An efficient stereoselective strategy for the synthesis of chiral bisspiro barbituric acid-oxindole derivatives was developed. The asymmetric Michael addition/cyclization tandem reaction between benzylidene barbituric acids and oxindolylmalonitriles was catalyzed by squaramide catalyst, and the corresponding spirocyclic products were obtained in good-to-high yields (up to 97%) with excellent stereoselectivities (up to >99% ee, >20:1 dr). At the same time, the practicality of the reaction was verified by the gram-scale preparation reaction.
View Article and Find Full Text PDF