Copper-catalyzed enantioselective coupling has been widely investigated, which allows rapid construction of various chiral molecules. Despite important advances polar and radical mechanisms, exploring general and practical strategies for the regio-, enantio- and diastereoselective assembly of stereogenic centers is of significant value but remains highly problematic. The integration of photocatalysis with asymmetric copper catalysis could provide appealing access to the development of new reaction pathways and structurally diverse chiral compounds, and extend the boundaries of radical chemistry. This review summarizes recent advances in photoinduced copper-catalyzed enantioselective coupling reactions, and discusses the mechanistic aspects.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/d2cs00734g | DOI Listing |
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 PDFJ 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 PDFOrg Lett
January 2025
Department of Chemistry, College of Science, China Agricultural University, 2 Yuanmingyuan West Road, Beijing 100193, P. R. China.
A three-component cascade boronation-dearomatization reaction of alkenes, a diboron compound, and a pyridinium salt is diclosed, affording chiral boron-containing 1,4-dihyropyridines in high yields (≤98%) and diastereoselectivity (≤10:1 dr), along with excellent enantioselectivity (typically >99% ee). The catalytic system performs efficiently at low catalyst loadings (1 mol %) and was tested with >50 examples, including some biologically active molecules.
View Article and Find Full Text PDFNat Commun
January 2025
Department of Chemistry, University of Science and Technology of China, Hefei, PR China.
This study presents a copper-catalyzed, substrate-controlled regio- and enantioselective intermolecular hydrosilylation method capable of accommodating a broad scope of alkenes and prochiral silanes. The approach offers an efficient and versatile pathway to generate enantioenriched linear and branched alkyl-substituted Si-stereogenic silanes. Key features of this reaction include mild reaction conditions, simple catalytic systems, compatibility with diverse substrates, high yields and enantioselectivities.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
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.
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!