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Intramolecular alkene–alkyne metathesis and 1,4-cis-hydrogenation as a stereocontrolled route to compounds with exocyclic double bonds

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Abstract

Intramolecular alkene-alkyne metathesis of diethyl (but-3-en-1-yl)(propargyl)malonate affords diethyl 3-vinylcyclohex-3-ene-1,1-dicarboxylate whose conjugated diene system was 1,4-cis-hydrogenated in the presence of η6-(naphthalene)chromium tricarbonyl. The exocyclic double bond of thus formed diethyl 3-ethylidenecyclohexane-1,1-dicarboxylate is strictly (E)-configured.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. A. Vasil’ev & E. P. Serebryakov

  2. Department of Chemistry, Uppsala University, BMC Box 576, 751 23, Uppsala, Sweden

    L. Engman

Authors
  1. A. A. Vasil’ev
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  2. L. Engman
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  3. E. P. Serebryakov
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Corresponding author

Correspondence to A. A. Vasil’ev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0169–0171, January, 2020.

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Vasil’ev, A.A., Engman, L. & Serebryakov, E.P. Intramolecular alkene–alkyne metathesis and 1,4-cis-hydrogenation as a stereocontrolled route to compounds with exocyclic double bonds. Russ Chem Bull 69, 169–171 (2020). https://doi.org/10.1007/s11172-020-2739-1

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  • DOI: https://doi.org/10.1007/s11172-020-2739-1

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