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Highly Position- and Enantioselective Catalytic Epoxidation of Polyolefins Mediated by a Chiral Mn Complex, Including a One-Step Conversion of Squalene to the ()-2,3-Epoxide, a Precursor of Natural Steroids and Terpenoids.
J Am Chem Soc
January 2025
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
Reported herein is the synthesis of a novel chiral dicarboxylic ligand for Mn(II) and the application of the Mn complex to the highly enantio- and position-selective epoxidation of C═C under mild conditions, even with polyolefinic substrates. A stereomechanistic basis for asymmetric induction is suggested.
View Article and Find Full Text PDFPhotoinduced Regiodivergent and Enantioselective Cross-Coupling of Glycine Derivatives with Hydrocarbon Feedstocks.
J Am Chem Soc
January 2025
Key Laboratory of Chemical Biology of Fujian Province, iChEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
Regiodivergent asymmetric synthesis represents a transformative strategy for the efficient generation of structurally diverse chiral products from a single set of starting materials, significantly enriching their enantiomeric composition. However, the design of radical-mediated regiodivergent and enantioselective reactions that can accommodate a wide range of functional groups and substrates has posed significant challenges. The obstacles primarily lie in switching the regioselectivity and achieving high enantiodiscrimination, especially when dealing with high-energy intermediates.
View Article and Find Full Text PDFChiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of 2,2-Disubstituted 2,3-Dihydro-4-quinolones from Isatins and 2'-Aminoacetophenones.
Org Lett
January 2025
Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Herein, we present the enantioselective synthesis of 2,3-dihydro-4-quinolones bearing chiral tetrasubstituted carbons from isatins and 2'-aminoacetophenones. The transformation is mediated by a chiral phosphoric acid catalyst and proceeds via an generated ketimine and subsequent enantioselective intramolecular cyclization. The methodology features a broad scope and functional group tolerance with yields and enantioselectivities of up to 99% and 98% ee.
View Article and Find Full Text PDFSurface Decoration of Cellulose With Trifluoromethylphenyl Substituted Thiourea: A Robust Hydrogen-Bonding Catalyst in Conjunction With L-Proline for the Asymmetric Direct Mannich Reaction.
Biopolymers
January 2025
Department of Chemistry, Faculty of Engineering and Science, Bursa Technical University, Bursa, Turkey.
Cellulose is one of the most abundant biopolymers in nature. Despite being the subject of research in various fields, it is not as famous as chitosan in catalyst design. Herein, a novel thiourea-functionalized cellulose (CTU-6) was synthesized as a robust hydrogen bonding catalyst with the degree of substitution (DS) of 0.
View Article and Find Full Text PDFFacile construction of distal and diversified tertiary and quaternary stereocenters.
Proc Natl Acad Sci U S A
December 2024
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409.
Article Synopsis
- Researchers are focused on developing new chiral pharmaceutical candidates, which requires innovative synthetic chemistry techniques.
- Achieving diverse and efficient construction of molecular structures with multiple chiral centers is a major objective in the field.
- The introduction of a new method, asymmetric chain-walking arylation, allows for the effective creation of multiple chiral centers in compounds, showing promise for future industrial applications.
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