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| http://dx.doi.org/10.1042/bj0330044 | DOI Listing |
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Copper-Catalyzed Successive Radical Reactions of Glycine Derivatives.
Org Lett
January 2025
Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China.
Here, we present a three-component successive radical addition strategy for the preparation of complex noncanonical α-amino acids from easily available glycine derivatives, alkenes, and aryl sulfonium salts via a copper-catalyzed photoredox-neutral catalytic cycle. The utility of this method is further demonstrated by its application in late-stage site-selective modifications of glycine residues in short peptides. It is worth noting that only 1 mol % copper catalyst is required in this reaction, demonstrating high catalytic efficiency.
View Article and Find Full Text PDFDual Photoredox and Copper-Catalyzed Asymmetric Remote C(sp)-H Alkylation of Hydroxamic Acid Derivatives with Glycine Derivatives.
J Org Chem
January 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Dual photoredox and copper-catalyzed remote asymmetric C(sp)-H alkylation of hydroxamic acid derivatives with glycine derivatives via a 1,5-hydrogen transfer (1,5-HAT) process has been realized. The reaction was characterized by redox-neutral and mild conditions, good yields, excellent enantioselectivity, and broad substrate scope. This protocol provides a straightforward and efficient strategy to prepare highly valuable enantioenriched noncanonical α-amino acids.
View Article and Find Full Text PDFEnantioselective Synthesis of Chiral β-Amino Phosphorus Derivatives via Nickel-Catalyzed Asymmetric Hydrogenation.
J Am Chem Soc
January 2025
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 PDFHighly Efficient Synthesis of α-Amino Acids via Electrocatalytic C-N Coupling Reaction Over an Atomically Dispersed Iron Loaded Defective TiO.
Adv Mater
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State Key Laboratory of Chem/Bio-Sensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, P. R. China.
The synthesis of α-amino acids via the electrocatalytic C-N coupling attracted extensive attention owing to the mild reaction conditions, controllable reaction parameters, and atom economy. However, the α-amino acid yield remains unsatisfying. Herein, the efficient electrocatalytic synthesis of α-amino acids is achieved with an atomically dispersed Fe loaded defective TiO monolithic electrocatalyst (Fe-TiO/Ti).
View Article and Find Full Text PDFSequential Photocatalysis for Homologative Diversification of α-Amino Acids to β-Amino Acids Via Phosphonium Ylide Linchpin Strategy.
J Am Chem Soc
December 2024
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo, Kyoto 606-8501, Japan.
β-Amino acids serve as crucial building blocks for a broad range of biologically active molecules and peptides with potential as peptidomimetics. While numerous methods have been developed for the synthesis of β-amino acids, most of them require multistep preparation of specific reagents and substrates, which limits their synthetic practicality. In this regard, a homologative transformation of abundant and readily available α-amino acids would be an attractive approach for β-amino acid synthesis.
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