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Rhodium-catalyzed intermolecular enantioselective Alder–ene type reaction of cyclopentenes with silylacetylenes

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  • Dongquan Zhang

    (China Pharmaceutical University)

  • Miaomiao Li

    (China Pharmaceutical University)

  • Jiajia Li

    (China Pharmaceutical University)

  • Aijun Lin

    (China Pharmaceutical University)

  • Hequan Yao

    (China Pharmaceutical University)

Abstract

The Alder–ene type reaction between alkenes and alkynes provides an efficient and atom-economic method for the construction of C-C bond, which has been widely employed in the synthesis of natural products and other functional molecules. The intramolecular enantioselective Alder-ene cycloisomerization reactions of 1,n-enynes have been extensively investigated. However, the intermolecular asymmetric version has not been reported, and remains a challenging task. Herein, we describe a rhodium-catalyzed intermolecular enantioselective Alder-ene type reaction of cyclopentenes with silylacetylenes. A variety of chiral (E)-vinylsilane tethered cyclopentenes bearing one quaternary carbon and one tertiary carbon stereocenters are achieved in high yields and enantioselectivities. The reaction undergoes carbonyl-directed migratory insertion, β-H elimination and desymmetrization of prochiral cyclopentenes processes.

Suggested Citation

  • Dongquan Zhang & Miaomiao Li & Jiajia Li & Aijun Lin & Hequan Yao, 2021. "Rhodium-catalyzed intermolecular enantioselective Alder–ene type reaction of cyclopentenes with silylacetylenes," Nature Communications, Nature, vol. 12(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-26955-9
    DOI: 10.1038/s41467-021-26955-9
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    References listed on IDEAS

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    1. Kyle W. Quasdorf & Larry E. Overman, 2014. "Catalytic enantioselective synthesis of quaternary carbon stereocentres," Nature, Nature, vol. 516(7530), pages 181-191, December.
    2. Ahmad Masarwa & Dorian Didier & Tamar Zabrodski & Marvin Schinkel & Lutz Ackermann & Ilan Marek, 2014. "Merging allylic carbon–hydrogen and selective carbon–carbon bond activation," Nature, Nature, vol. 505(7482), pages 199-203, January.
    3. Tian-Sheng Mei & Harshkumar H. Patel & Matthew S. Sigman, 2014. "Enantioselective construction of remote quaternary stereocentres," Nature, Nature, vol. 508(7496), pages 340-344, April.
    4. Zhenbo Yuan & Yuye Zeng & Ziwen Feng & Zhe Guan & Aijun Lin & Hequan Yao, 2020. "Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
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