Enantioselective Synthesis of Cyclohepta[b]indoles via Pd-Catalyzed Cyclopropane C(sp3)-H Activation as a Key Step
Enantioselective Synthesis of Cyclohepta[b]indoles via Pd-Catalyzed Cyclopropane C(sp3)-H Activation as a Key Step
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2019
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Organic Letters ; 21 (2019), 18. - pp. 7370-7374. - ISSN 1523-7060. - eISSN 1523-7052
Abstract
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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HÄFNER, 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. 21(18), pp. 7370-7374. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.9b02687BibTex
@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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