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Budynina EM, Ivanov KL, Chagarovskiy AO, et al. From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes. Chemistry. 2016;22(11):3692-6doi: 10.1002/chem.201504593.
Budynina, E. M., Ivanov, K. L., Chagarovskiy, A. O., Rybakov, V. B., Trushkov, I. V., & Melnikov, M. Y. (2016). From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes. Chemistry (Weinheim an der Bergstrasse, Germany), 22(11), 3692-6. https://doi.org/10.1002/chem.201504593
Budynina, Ekaterina M, et al. "From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,11 (2016): 3692-6. doi: https://doi.org/10.1002/chem.201504593
Budynina EM, Ivanov KL, Chagarovskiy AO, Rybakov VB, Trushkov IV, Melnikov MY. From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes. Chemistry. 2016 Mar 07;22(11):3692-6. doi: 10.1002/chem.201504593. Epub 2016 Feb 16. PMID: 26880270.
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Chemistry. 2016 Mar 07;22(11):3692-6. doi: 10.1002/chem.201504593. Epub 2016 Feb 16.

From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ekaterina M Budynina, Konstantin L Ivanov, Alexey O Chagarovskiy, Victor B Rybakov, Igor V Trushkov, Mikhail Ya Melnikov

Affiliations

  1. Moscow State University, Department of Chemistry, Leninskie gory, Moscow, 119991, Russian Federation. [email protected].
  2. Moscow State University, Department of Chemistry, Leninskie gory, Moscow, 119991, Russian Federation.
  3. Federal Research Center of Pediatric Hematology, Oncology and Immunology, Laboratory of Chemical Synthesis, Samory Mashela, Moscow, 117997, Russian Federation.

PMID: 26880270 DOI: 10.1002/chem.201504593

Abstract

A conceptually new type of donor-acceptor cyclopropane reactivity towards nucleophiles has been disclosed. An essential characteristic of the process is an unusual nucleophilic attack on the C(3)-position of a cyclopropane, combined with typical small ring-opening by cleavage of the C(1)-C(2) bond between the acceptor and the donor. Based on this new reaction between cyclopropane-1,1-diesters and nitroalkanes, we developed a convenient approach to γ-nitroesters that can be efficiently transformed to the substituted pyrrolidones, structural analogues of racetame family drugs (rolipram, phenylpiracetam, etc.).

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: heterocyclic compounds; nitro compounds; nucleophilic addition; pyrrolidones; small rings

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