Cinchona alkaloids were used as Lewis base catalysts in the title reaction. The [4+2] cyclization of α,β-unsaturated acyl chlorides with electron-deficient alkenes derived from oxindole gave the corresponding spirocarbocyclic oxindoles.
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http://dx.doi.org/10.1002/anie.201207405 | DOI Listing |
J Am Chem Soc
January 2025
Molecular Synthesis Center, Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
2-Deoxy-β-glycosides are essential components of natural products and pharmaceuticals; however, the corresponding 2-deoxy-β-glycosidic bonds are challenging to chemically construct. Herein, we describe an efficient catalytic protocol for synthesizing 2-deoxy-β-glycosides via either IPrAuNTf-catalyzed activation of a unique 1,2--positioned C2--propargyl xanthate (OSPX) leaving group or (PhO)PAuNTf-catalyzed activation of a 1,2--C2--alkynylbenzoate (OABz) substituent of the corresponding thioglycosides. These activation processes trigger 1,2-alkyl/arylthio-migration glycosylation, enabling the synthesis of structurally diverse 2-deoxy-β-glycosides under mild reaction conditions.
View Article and Find Full Text PDFOrg Lett
January 2025
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.
The catalytic asymmetric multicomponent acylation/rearrangement/cyclization of alkenylfurans with acyl oxime esters/arylamines or acyl oxime esters/arylamines/hydroxylamine has been developed. This method employs synergistic photoredox/Brønsted acid catalysis, enabling the efficient and versatile synthesis of multifunctionalized [3.2.
View Article and Find Full Text PDFChem Asian J
January 2025
East China University of Science and Technology, Institute of Fine Chemicals, Meilong Road, 200237, Shanghai, CHINA.
Oxidation of thia-pentapyrrane S-P4 with terminal β-linked pyrrole and thiophene units in the presence of various metal ions has been found to afford distinct porphyrinoids. Specifically, N-confused thiasapphyrin (1), Cu(III) norrole (2), neo-confused phlorin (3), and p-benzinorrole (4) were obtained, when S-P4 was oxidized with p-chloranil in acetonitrile in the presence of Ni2+, Cu2+, Cd2+, and Co2+, respectively. The structures of 1-4 have been clearly elucidated by NMR spectroscopy, HRMS, and X-ray crystal diffraction (for 2-4).
View Article and Find Full Text PDFMolecules
January 2025
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, Republic of Korea.
A thiazolo-pyrimidinone derivative library was developed through a facile solid-phase synthesis method. For the reaction, the thiazolo[4,5-]pyrimidin-7(6)-one structure was synthesized through efficient Thorpe-Ziegler and cyclization reactions. The thiazolo[4,5-]pyrimidin-7(6)-one derivative library with a diversity of three had a total of four synthesis steps and 57 compounds.
View Article and Find Full Text PDFOrg Lett
January 2025
Engineering Research Center of Ministry of Education for Fine Chemicals, Shanxi University, Taiyuan 030006, P. R. of China.
Herein a novel and robust methodology to spiroimidazolidinones has been developed under a mild reaction. The reaction of (Z)-2-azido-3-phenylacrylic acids , aldehydes , amines , isocyanides , and isocyanides produced regioselectively spiroimidazolidinones in 71-88% yields via a sequential Ugi 4CR/Pd(0) catalyzed azide-isocyanide coupling/cyclization/rearrangement/hydroxylation reaction. Furthermore, the easily accessible starting materials, high bond-forming efficiency, and broad substituent tolerance make this strategy useful in synthetic and medicinal chemistry.
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