V. A. Ikonnikova, E. A. Zhigileva, A. V. Kuleshov, V. V. Shirokova, M. S. Baranov, A. A. Mikhaylov, “Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols”, Mendeleev Commun., 2021, Volume 31, Issue 5,Pages <nobr>657

This article is cited in 5 papers

Communications

Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols

V. A. Ikonnikova^ab, E. A. Zhigileva^ac, A. V. Kuleshov^ac, V. V. Shirokova^ab, M. S. Baranov^a, A. A. Mikhaylov^a

^a M.M. Shemyakin–Yu.A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b Higher Chemical College of the Russian Academy of Sciences, D.I. Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
^c Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation

Abstract: Imidazolone-activated donor–acceptor cyclopropanes undergo alcohol-assisted ring opening under the co-action of p-toluenesulfonic acid. Under the optimized conditions, cyclopropanes and alcohols are coupled in 1,3-fashion with the retention of heterocyclic fragment. Substrates with aromatic donor groups provide the addition products in 75–99% yields as mixtures of two diastereomers.

Keywords: donor–acceptor cyclopropanes, spirocyclic compounds, imidazolones, alcohols, nucleophilic ring opening.

Language: English

DOI: 10.1016/j.mencom.2021.09.021

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