ArticleNature communications2023
Rhodium-catalyzed enantioselective and diastereodivergent access to diaxially chiral heterocycles.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Enantioselective Synthesis of Axially Chiral Diaryl Ethers via Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Enantioselective Iridium-Catalyzed C-H Bond Alkylation for the Synthesis of N-N Atropisomeric Phosphines.Journal of the American Chemical Society · 2026Article
- Recent Advances in the Synthesis of C-N/N-N Atropisomers via Asymmetric Annulation.Topics in current chemistry (Cham) · 2026Review
- Recent advances in the stereoselective synthesis of distal biaxially chiral molecules.Beilstein journal of organic chemistry · 2026Review
- Copper-catalyzed atroposelective hydroarylation of 1-alkynylindoles.Nature communications · 2025Article
- Asymmetric synthesis of chiral boronic esters featuring nonadjacent axial and flexible, acyclic central chirality.Science advances · 2025Article
- Rhodium-catalyzed construction of boron-based point and axial chirality via asymmetric annulation of alkynylborons.Nature communications · 2025Article
- Atroposelective [4+1] annulation for the synthesis of isotopic isoindolinones bearing both central and axial chirality.Chemical science · 2025Article
- Organocatalyzed diastereo- and enantioselective synthesis of N-N atropisomeric isoindolinones bearing central chirality.Nature communications · 2025Article
- Simultaneous construction of inherent and axial chirality by cobalt-catalyzed enantioselective C-H activation of calix[4]arenes.Nature communications · 2024Article
- Access to distal biaxial atropisomers by iridium catalyzed asymmetric C-H alkylation.Chemical science · 2024Article
- Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis.Chemical science · 2024Article
- Copper-catalysed asymmetric annulation of yne-allylic esters with amines to access axially chiral arylpyrroles.Nature communications · 2024Article
- Pd-catalyzed asymmetric Larock reaction for the atroposelective synthesis of N─N chiral indoles.Science advances · 2024Article
- Ir/Zn-cocatalyzed chemo- and atroposelective [2+2+2] cycloaddition for construction of C─N axially chiral indoles and pyrroles.Science advances · 2023Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
N-N axially chiral biaryls represent a rarely explored class of atropisomers. Reported herein is construction of diverse classes of diaxially chiral biaryls containing N-N and C-N/C-C diaxes in distal positions in excellent enantioselectivity and diastereoselectivity. The N-N chiral axis in the products provides a handle toward solvent-driven diastereodivergence, as has been realized in the coupling of a large scope of benzamides and sterically hindered alkynes, affording diaxes in complementary diastereoselectivity. The diastereodivergence has been elucidated by computational studies which revealed that the hexafluoroisopropanol (HFIP) solvent molecule participated in an unusual manner as a solvent as well as a ligand and switched the sequence of two competing elementary steps, resulting in switch of the stereoselectivity of the alkyne insertion and inversion of the configuration of the C-C axis. Further cleavage of the N-directing group in the diaxial chiral products transforms the diastereodivergence to enantiodivergence.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.