The enantioselective synthesis of tricyclic oxoquinolines NHC-catalyzed cascade reaction of enals with malonates bearing a 2-aminophenyl group is reported. The chiral α,β-unsaturated acylazoliums underwent a smooth Michael-aldol-lactamization-dehydration quadruple cascade with the amino malonate derivative to afford the desired tricyclic products.
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http://dx.doi.org/10.1039/d4cc00502c | DOI Listing |
J Agric Food Chem
December 2024
College of Plant Protection, Southwest University, Chongqing 400715, China.
Etoxazole, a widely used mite growth inhibitor, contains a chiral center in its chemical structure, resulting in two mirror-image enantiomers. These enantiomers of etoxazole display significant differences in biological activity and environmental behavior. In bioassays conducted against , it was observed that S-etoxazole demonstrated approximately 279.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
Compared with chiral β-amino phosphorus compounds, which can be easily derived from natural optically pure α-amino acids, obtaining chiral β-amino phosphorus derivatives remains a challenge. These derivatives, which cannot be derived from chiral natural amino acids, possess unique biological activities or potential catalytic activities. Herein, highly enantioselective hydrogenation for the preparation of chiral β-amino phosphorus derivatives from -β-enamido phosphorus compounds is reported by using a green and low-cost earth-abundant metal nickel catalyst (13 examples of 99% ee).
View Article and Find Full Text PDFAppl Microbiol Biotechnol
December 2024
Department of Life Science and Technology: Tokyo Kogyo Daigaku Seimei Rikogakuin Seimei Rikogakukei, Institute of Science Tokyo, 4259 Nagatsuta-Cho Midzeori-Ku, Yokohama, 226-8501, Japan.
Chiral diaryl alcohols, such as (4-chlorophenyl)(pyridin-2-yl)methanol, are important intermediates for pharmaceutical synthesis. However, using alcohol dehydrogenases (ADHs) in the asymmetric reduction of diaryl ketones to produce the corresponding alcohols is challenging due to steric hindrance in the substrate binding pockets of the enzymes. In this study, the steric hindrance of the ADH from Geotrichum candidum NBRC 4597 (G.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100, China.
Catalytic asymmetric transformation of donor-acceptor cyclopropanes (DACs) has been proven to be a highly valuable and robust strategy to construct diverse types of enantioenriched molecules. However, the use of 1,1,2,2-tetrasubstituted DACs to form products bearing quaternary stereocenters remains a long-term unsolved challenge. Here, we report the copper-catalyzed asymmetric aminative ring opening of tetrasubstituted alkynyl DACs that delivers a myriad of α-tertiary amines with high levels of enantioselectivities.
View Article and Find Full Text PDFJ Org Chem
December 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China.
A palladium-catalyzed asymmetric chlorocyclization of 1,6-enynes has been described. Controlling the chloride ion concentration in the system by substrate design is the key to achieving asymmetric chlorinated cyclization. In the presence of Pd(PhCN)Cl and chiral phosphoramidite ligands, the reaction accesses diverse chiral ()-α-chloromethylene-γ-butyrolactams with excellent selectivity and enantioselectivity.
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