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Novel C2-symmetric phenylglycine derivatives as organocatalysts of the Michael reaction between nitroalkenes and ketones

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Abstract

A comprehensive study of the activity of the amide-type organocatalysts based on (R)- and (S)-phenylglycine and 1,2-di(2-pyridyl)-1,2-diaminoethane in the asymmetric Michael reaction between various nitroalkenes and ketones was carried out. The products of the studied reactions were formed in up to 99% yield, with syn diastereoselectivity (dr) >20: 1 and enantiomeric excess of up to 93% ee for syn-isomer. The organocatalysts can be regenerated and reused in at least seven reaction cycles.

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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. Kostenko, O. Yu. Kuznetsova, A. S. Kucherenko & S. G. Zlotin

Authors
  1. A. A. Kostenko
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  2. O. Yu. Kuznetsova
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  3. A. S. Kucherenko
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  4. S. G. Zlotin
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Corresponding author

Correspondence to A. S. Kucherenko.

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Dedicated to Academician of the Russian Academy of Sciences V. N. Charushin on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 885–889, May, 2021.

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Kostenko, A.A., Kuznetsova, O.Y., Kucherenko, A.S. et al. Novel C2-symmetric phenylglycine derivatives as organocatalysts of the Michael reaction between nitroalkenes and ketones. Russ Chem Bull 70, 885–889 (2021). https://doi.org/10.1007/s11172-021-3163-x

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  • DOI: https://doi.org/10.1007/s11172-021-3163-x

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