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Amide-Directed Highly Enantioselective Hydrogenation of Diverse Acyclic Multisubstituted Alkenes Under Mild Conditions.
Angew Chem Int Ed Engl
January 2025
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084, China.
Enantioselective hydrogenation of tetrasubstituted alkenes to form 1,2-contiguous stereocenters is a particularly appealing but highly challenging transformation in asymmetric catalysis. Despite the notable progress achieved in enantioselective hydrogenation over the past decades, enantioselective hydrogenation of all-carbon tetrasubstituted alkenes containing multiple alkyl groups remains an unsolved challenge. Here, we report a rhodium-catalyzed highly diastereo- and enantioselective hydrogenation of diverse acyclic multisubstituted alkenes under mild conditions.
View Article and Find Full Text PDFRhodium-Catalyzed Asymmetric Reductive Hydroformylation of α-Substituted Enamides.
J Am Chem Soc
December 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
Chiral γ-amino alcohols are prevalent structural motifs in natural products and bioactive compounds. Nevertheless, efficient and atom-economical synthetic methods toward enantiomerically enriched γ-amino alcohols are still lacking. In this study, a highly enantioselective rhodium-catalyzed reductive hydroformylation of readily available α-substituted enamides is developed, providing a series of pharmaceutically valuable chiral 1,3-amino alcohols in good yields and excellent enantioselectivities in a single step.
View Article and Find Full Text PDFRhodium-Catalyzed Meta-C-H Arylation of Arenes with Varied Linker Lengths: Bridging Catalytic Selectivity with Structural Diversity.
Angew Chem Int Ed Engl
November 2024
Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, 400076, India.
The directing group (DG)-assisted approach has so far been the major route to achieve selective C-H activation at both proximal and distal positions. While rhodium catalysts are highly effective in DG-assisted ortho-C-H arylation, meta-C-H arylation with rhodium has not yet been reported. In this study, we present the first example of Rh-catalyzed meta-C-H arylation of arenes.
View Article and Find Full Text PDFModular synthesis of triphenylphosphine-derived cage ligands for rhodium-catalyzed hydroformylation applications.
Dalton Trans
December 2024
Dalian National Laboratory for Clean Energy and State Key Laboratory of catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Four new triphenylphosphine-derived cage ligands were modularly synthesized dynamic imine chemistry (DIC), and their absolute structures were characterized by single crystal X-ray diffraction (SXRD), nuclear magnetic resonance (NMR) and high resolution mass spectroscopy (HRMS). In contrast to small-molecule analogues, cage ligands demonstrate superior activity and selectivity. The Rh/Cage-L2 catalyst exhibits remarkable performance with an aldehyde selectivity of 89%, accompanied by a TOF value of 2665 h and an / ratio of 2.
View Article and Find Full Text PDFRhodium-catalyzed synthesis of Si-stereogenic alkoxysilanes and silyl enol ethers hydrosilylation of carbonyl compounds.
Chem Commun (Camb)
November 2024
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China.
A highly efficient rhodium-catalyzed asymmetric hydrosilylation of aldehydes, ketones, and α,β-unsaturated ketones with dihydrosilanes is developed, that allows the rapid assembly of a variety of Si-stereogenic alkoxysilanes and silyl enol ethers in good yields and enantioselectivities under mild conditions. The applicability of this methodology was demonstrated by a series of stereospecific transformations to construct diverse Si-stereogenic derivatives.
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