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Stereochemistry of the Horner-Emmons reaction of 3-functionalized 2-methyl-2-propenylphosphonates with aliphatic aldehydes. 1. Effect of size of the alkoxy group attached to the phosphorus atom

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The first step in the Homer-Emmons reaction of isovaleraldehyde with a 3-alkoxycarbonyl-2-methyl-2-propenylphosphonate in the presence of KOH involves rapid “stereomutation” of the phosphonate, resulting in an equilibrium mixture with the Z-isomer predominating; the quantitative composition of this mixture does not depend on the ratio of E- and Z-isomers in the phosphonate starting material.

  2. 2.

    As the size (volume) of the alkoxy substituents attached to the phosphorus atom is increased in the phosphonate starting material the fraction of the (2E, 4E)-stereoisomer in the product 3,7-dimethyl-2,4-octadienoate ester also increases, in the order MeO < EtO < i-PrO.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    G. V. Kryshtal', É. P. Serebryakov, L. M. Suslova & L. A. Yanovskaya

Authors
  1. G. V. Kryshtal'
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  2. É. P. Serebryakov
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  3. L. M. Suslova
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  4. L. A. Yanovskaya
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2377–2382, October, 1988.

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Kryshtal', G.V., Serebryakov, É.P., Suslova, L.M. et al. Stereochemistry of the Horner-Emmons reaction of 3-functionalized 2-methyl-2-propenylphosphonates with aliphatic aldehydes. 1. Effect of size of the alkoxy group attached to the phosphorus atom. Russ Chem Bull 37, 2142–2146 (1988). https://doi.org/10.1007/BF00953422

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  • DOI: https://doi.org/10.1007/BF00953422

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