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Enantioselective Synthesis of Cyclohepta[b]indoles via Pd-Catalyzed Cyclopropane C(sp3)-H Activation as a Key Step

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https://doi.org/10.1021/acs.orglett.9b02687
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Organic Letters. 2019, 21(18), pp. 7370-7374. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.9b02687

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An enantioselective synthesis of functionalized cyclohepta[b]indoles via Pd-catalyzed cyclopropane C-H activation followed by olefination and indole-vinylcyclopropane rearrangement is reported. The design of the chiral cyclopropane precursor was such that both enantiomeric cyclohepta[b]indoles were accessed from a single compound exhibiting a "hidden" symmetry plane. The scope of the method was demonstrated by varying the substituents on the cyclopropane as well as on the heterocycle itself.

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ISO 690HÄFNER, Maximilian, Yevhenii M. SOKOLENKO, Paul GAMERDINGER, Erik STEMPEL, Tanja GAICH, 2019. Enantioselective Synthesis of Cyclohepta[b]indoles via Pd-Catalyzed Cyclopropane C(sp3)-H Activation as a Key Step. In: Organic Letters. 2019, 21(18), pp. 7370-7374. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.9b02687
BibTex
@article{Hafner2019-09-20Enant-47048,
  year={2019},
  doi={10.1021/acs.orglett.9b02687},
  title={Enantioselective Synthesis of Cyclohepta[b]indoles via Pd-Catalyzed Cyclopropane C(sp<sup>3</sup>)-H Activation as a Key Step},
  number={18},
  volume={21},
  issn={1523-7060},
  journal={Organic Letters},
  pages={7370--7374},
  author={Häfner, Maximilian and Sokolenko, Yevhenii M. and Gamerdinger, Paul and Stempel, Erik and Gaich, Tanja}
}
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