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Copper(II)-Catalyzed Asymmetric (3+3) Annulation of Diaziridines with Oxiranes.
Org Lett
January 2025
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Highly asymmetric (3+3) annulation of diaziridines with oxiranes via C-N bond cleavage in diaziridine was achieved under 10 mol % of chiral copper(II) complex as the catalyst under mild reaction conditions. With Cu(OTf) as the Lewis acid and C-symmetric imidazolidine-pyrroloimidazolone pyridine as the ligand, diverse tetrahydro-[1,3,4]-oxadiazines were obtained by stereospecific C-N/C-O bond formation in moderate to good yields (up to 93% yield) and high diastereo- (>20:1 dr) and enantioselectivities (up to 92% ee). The catalytic cycle and stereochemical model were proposed by DFT calculation.
View Article and Find Full Text PDFEnantioselective Catalytic Synthesis of Inherently Chiral Calixarenes.
Chem Rec
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
Since the introduction of the concept of inherent chirality by Böhmer, an important part of research focused on the asymmetric synthesis of calixarene macrocycles. However, long synthetic procedures and tedious separation strategies hampered the application of this technology in many topics of organic chemistry, including enantioselective molecular recognition and catalysis. Very recently, a new generation of enantioselective catalytic methodologies has been reported, able to provide highly functionalized, inherently chiral calixarenes in a straightforward manner.
View Article and Find Full Text PDFEnantioselective Borylcupration/Cyclization of Alkene-Tethered Oxime Esters.
Angew Chem Int Ed Engl
January 2025
University of Toronto, Dept. of Chemistry, 80 St. George Street, M5S 3H6, Toronto, CANADA.
A copper-catalyzed enantioselective synthesis of borylated 1-pyrrolines from γ,δ-unsaturated oxime esters is reported. Twenty-four novel 1-pyrroline derivatives are reported in yields ranging from 26% to 96% and enantioselectivities from 74.5:25.
View Article and Find Full Text PDFStereodivergent Construction of 3,3'-Disubstituted Oxindoles via One-Pot Sequential Allylation/Alkylation and Its Application to the Total Synthesis of Trigolute B and D.
J Am Chem Soc
January 2025
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.
The absolute and relative configurations of bioactive chiral molecules are typically relevant to their biological properties. It is thus highly important and desirable to construct all possible stereoisomers of a lead candidate or a given bioactive natural compound. Synergistic dual catalysis has been recognized as a reliable synthetic strategy for a variety of predictable stereodivergent transformations.
View Article and Find Full Text PDFCatalytic asymmetric photocycloaddition reactions mediated by enantioselective radical approaches.
Chem Soc Rev
January 2025
Pingyuan Laboratory, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, Henan, P. R. China.
The use of olefins in the construction of cyclic compounds represents a powerful strategy for advancing the pharmaceutical industry. Photocycloaddition has attracted significant interest from chemists due to its ability to exploit simple and readily available olefins along with their reaction patterns under mild conditions. Moreover, the sustainable and versatile pathways for generating highly reactive intermediates can greatly enrich both substrate diversity and reaction patterns.
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