Stereocontrolled Synthesis of Chiral Helicene-Indenido ansa- and Half-Sandwich Metal Complexes and Their Use in Catalysis

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F25%3A00601116" target="_blank" >RIV/61388963:_____/25:00601116 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1002/anie.202414698" target="_blank" >https://doi.org/10.1002/anie.202414698</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/anie.202414698" target="_blank" >10.1002/anie.202414698</a>

Result language
angličtina
Original language name
Stereocontrolled Synthesis of Chiral Helicene-Indenido ansa- and Half-Sandwich Metal Complexes and Their Use in Catalysis
Original language description
Despite recent tremendous progress in the synthesis of nonplanar chiral aromatics, and helicenes in particular, their conversion to half-sandwich or sandwich transition metal complexes still lags behind, although they represent an attractive family of modular and underexplored chiral architectures with a potential catalytic use. In this work, starting from various chiral helicene-indene proligands, we prepared the enantio- and diastereopure oxa[6]- and oxa[7]helicene-indenido half-sandwich RhI and RhIII complexes and oxa[7]helicene-bisindenido ansa-metallocene FeII complex. To document their use, oxahelicene-indenido half-sandwich RhIII complexes were employed as chiral catalysts in enantioselective C-H arylation of benzo[h]quinolines with 1-diazonaphthoquinones to afford a series of axially chiral biaryls in mostly good to high yields and in up to 96:4 er. Thus, we developed stereocontrolled synthesis of chiral helicene-indenido ansa- and half-sandwich metal complexes, successfully demonstrated the first use of such helicene Cp-related metal complexes in enantioselective catalysis, and described an unusual sequence of efficient central-to-helical-to-planar-to-axial chirality transfer.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA22-18773S" target="_blank" >GA22-18773S: Helically chiral ligands for asymmetric transition metal catalysis</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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