title: From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes.
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.).
authors.affiliation: Moscow State University, Department of Chemistry, Leninskie gory, Moscow, 119991, Russian Federation. ekatbud@kinet.chem.msu.ru.
authors.forename: Ekaterina M
authors.initials: EM
authors.lastname: Budynina
authors.affiliation: Moscow State University, Department of Chemistry, Leninskie gory, Moscow, 119991, Russian Federation.
authors.forename: Konstantin L
authors.initials: KL
authors.lastname: Ivanov
authors.affiliation: Moscow State University, Department of Chemistry, Leninskie gory, Moscow, 119991, Russian Federation.|Federal Research Center of Pediatric Hematology, Oncology and Immunology, Laboratory of Chemical Synthesis, Samory Mashela, Moscow, 117997, Russian Federation.
authors.forename: Alexey O
authors.initials: AO
authors.lastname: Chagarovskiy
authors.affiliation: Moscow State University, Department of Chemistry, Leninskie gory, Moscow, 119991, Russian Federation.
authors.forename: Victor B
authors.initials: VB
authors.lastname: Rybakov
authors.affiliation: Moscow State University, Department of Chemistry, Leninskie gory, Moscow, 119991, Russian Federation.|Federal Research Center of Pediatric Hematology, Oncology and Immunology, Laboratory of Chemical Synthesis, Samory Mashela, Moscow, 117997, Russian Federation.
authors.forename: Igor V
authors.initials: IV
authors.lastname: Trushkov
authors.affiliation: Moscow State University, Department of Chemistry, Leninskie gory, Moscow, 119991, Russian Federation.
authors.forename: Mikhail Ya
authors.initials: MY
authors.lastname: Melnikov
keywords: heterocyclic compounds; nitro compounds; nucleophilic addition; pyrrolidones; small rings