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Peer-reviewedCC BY 4.0ACS Central Science

Enantioselective Access to the Parent Helicenols by Kinetic Resolution through Cu–H-Catalyzed Si–O Coupling

  • Lisa A. Böser1
  • Arthur M. J. David1
  • Elisabeth Irran1
  • Martin Oestreich1
  1. 1Technische Universität Berlin , , Strasse des 17. Juni 115 , ,
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Abstract

A Cu–H-catalyzed kinetic resolution of the parent [n]helicenols (n = 5, 6) through enantioselective dehydrogenative silylation with a secondary silane is reported. The dihydrosilane eventually employed is prochiral, thereby simultaneously establishing stereogenicity at the silicon atom as part of the resolution. The method provides highly enantioenriched helicenols and reveals a pronounced structure-selectivity relationship. Among the obtained products is a previously unknown, enantioenriched triflate-functionalized helicenol that enables further diversification through cross-coupling reactions.

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Cite

BibTeXRIS
BibTeX
@article{boser2026enantioselective,
  title = {{Enantioselective Access to the Parent Helicenols by Kinetic Resolution through Cu–H-Catalyzed Si–O Coupling}},
  author = {Lisa A. Böser and Arthur M. J. David and Elisabeth Irran and Martin Oestreich},
  journal = {ACS Central Science},
  year = {2026},
  month = oct,
  doi = {10.1021/acscentsci.6c01317},
  url = {https://pubs.acs.org/acscii/article/doi/10.1021/acscentsci.6c01317/5445596/Enantioselective-Access-to-the-Parent-Helicenols},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Enantioselective Access to the Parent Helicenols by Kinetic Resolution through Cu–H-Catalyzed Si–O Coupling
AU  - Lisa A. Böser
AU  - Arthur M. J. David
AU  - Elisabeth Irran
AU  - Martin Oestreich
PY  - 2026
DA  - 2026/10/06
JO  - ACS Central Science
DO  - 10.1021/acscentsci.6c01317
UR  - https://pubs.acs.org/acscii/article/doi/10.1021/acscentsci.6c01317/5445596/Enantioselective-Access-to-the-Parent-Helicenols
AB  - A Cu–H-catalyzed kinetic resolution of the parent [n]helicenols (n = 5, 6) through enantioselective dehydrogenative silylation with a secondary silane is reported. The dihydrosilane eventually employed is prochiral, thereby simultaneously establishing stereogenicity at the silicon atom as part of the resolution. The method provides highly enantioenriched helicenols and reveals a pronounced structure-selectivity relationship. Among the obtained products is a previously unknown, enantioenriched triflate-functionalized helicenol that enables further diversification through cross-coupling reactions.
SN  - 2374-7943
SN  - 2374-7951
ER  -