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Reactions of diazo esters with electron-deficient alkenes in the presence of Lewis acids

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Abstract

1,3-Dipolar cycloaddition reaction of diazo esters to electron-deficient dipolarophiles to yield the corresponding 1- or 2-pyrazolines was found to be significantly accelerated with Lewis acids (Yb(OTf)3, Sc(OTf)3, GaCl3, EtAlCl2). The use of GaCl3 as the catalyst leads to the acceleration not only of the 1,3-dipolar cycloaddition reaction, but also subsequent insertion of the CHCO2Me electrophilic fragment of methyl diazoacetate into the N-H bond of 2-pyrazolines formed. Such Lewis acids as SnCl4, BF3, TiCl4, and In(OTf)3 are not efficient in the described processes, since they rapidly decompose starting diazo compounds.

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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

    R. A. Novikov, D. N. Platonov, Yu. V. Tomilov & O. M. Nefedov

  2. Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    V. A. Dokichev

Authors
  1. R. A. Novikov
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  2. D. N. Platonov
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  3. V. A. Dokichev
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  4. Yu. V. Tomilov
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  5. O. M. Nefedov
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Corresponding author

Correspondence to Yu. V. Tomilov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 963–969, May, 2010.

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Novikov, R.A., Platonov, D.N., Dokichev, V.A. et al. Reactions of diazo esters with electron-deficient alkenes in the presence of Lewis acids. Russ Chem Bull 59, 984–990 (2010). https://doi.org/10.1007/s11172-010-0194-0

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  • DOI: https://doi.org/10.1007/s11172-010-0194-0

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