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Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines

Author

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  • Kun Xu

    (Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg)

  • Thomas Gilles

    (Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg)

  • Bernhard Breit

    (Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg)

Abstract

The asymmetric synthesis of N-allylic indoles is important for natural product synthesis and pharmaceutical research. The regio- and enantioselective N-allylation of indoles is a true challenge due to the favourable C3-allylation. We develop here a new strategy to the asymmetric synthesis of N-allylic indoles via rhodium-catalysed N-selective coupling of aryl hydrazines with allenes followed by Fischer indolization. The exclusive N-selectivities and good to excellent enantioselectivities are achieved applying a rhodium(I)/DTBM-Segphos or rhodium(I)/DTBM-Binap catalyst. This method permits the practical synthesis of valuable chiral N-allylated indoles, and avoids the N- or C-selectivity issue.

Suggested Citation

  • Kun Xu & Thomas Gilles & Bernhard Breit, 2015. "Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines," Nature Communications, Nature, vol. 6(1), pages 1-7, November.
    • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms8616
    DOI: 10.1038/ncomms8616
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    Cited by:

    1. Jiangtao Ren & Zheng Sun & Shuang Zhao & Jinyuan Huang & Yukun Wang & Cheng Zhang & Jinhai Huang & Chenhao Zhang & Ruipu Zhang & Zhihan Zhang & Xu Ji & Zhihui Shao, 2024. "Enantioselective synthesis of chiral α,α-dialkyl indoles and related azoles by cobalt-catalyzed hydroalkylation and regioselectivity switch," Nature Communications, Nature, vol. 15(1), pages 1-14, December.

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