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Stereoselective functionalization of 1-alkoxy-2-(phenylethynyl)cyclopropanes via lithiation and subsequent reactions with electrophilic reagents

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Abstract

trans-1-Alkoxy-2-(phenylethynyl)cyclopropanes undergo lithiation at the hydrogen atom in the α-position to the triple bond on treatment with BuLi in THF at–(65—70) °C. The resulting organolithium derivatives react with acetaldehyde, acetone, dimethyl disulfide, and methyl chloroformate giving the corresponding alcohols, sulfides, and esters with the yields up to 69% with complete retention of cyclopropane ring stereoconfiguration. The obtained methyl 3-alkoxy-2,2-dimethyl-1-(phenylethynyl)cyclopropanecarboxylates and the corre-sponding acid readily undergo ring opening with addition of water molecule or HCl.

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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

    V. D. Gvozdev, K. N. Shavrin & O. M. Nefedov

  2. Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    A. A. Ageshina

Authors
  1. V. D. Gvozdev
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  2. K. N. Shavrin
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  3. A. A. Ageshina
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  4. O. M. Nefedov
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Correspondence to V. D. Gvozdev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 0862—0866, May, 2017.

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Gvozdev, V.D., Shavrin, K.N., Ageshina, A.A. et al. Stereoselective functionalization of 1-alkoxy-2-(phenylethynyl)cyclopropanes via lithiation and subsequent reactions with electrophilic reagents. Russ Chem Bull 66, 862–866 (2017). https://doi.org/10.1007/s11172-017-1819-3

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  • DOI: https://doi.org/10.1007/s11172-017-1819-3

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