IMIDAZOLONE-ACTIVATED DONOR-ACCEPTOR CYCLOPROPANES WITH A PERIPHERAL STEREOCENTER. A STUDY ON STEREOSELECTIVITY OF CYCLOADDITION WITH ALDEHYDES

Authors

  • Андрей А. Михайлов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia
  • Павел Н. Сольев Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilova St., Moscow 119991, Russia
  • Андрей В. Кулешов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia Moscow Lomonosov State University, 1, Build. 3 Leninskie Gory, Moscow 119991, Russia
  • Вадим С. Кублицкий Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia
  • Александр А. Корлюков A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991, Russia
  • Владислав А. Лушпа Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia
  • Михаил С. Баранов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia

DOI:

https://doi.org/10.1007/5879

Keywords:

donor-acceptor cyclopropanes, imidazole, spirocyclic compounds, chirality, diastereoselectivity.

Abstract

Nucleophilic cyclopropanation of arylideneimidazolones possessing a peripheral chiral center and the subsequent fractional crystallization of diastereomers allows access to the compounds with an enantiomerically uniform configuration of the spirocyclic donoracceptor cyclopropane fragment. They were used to study the mechanism of the cycloaddition reaction with aldehydes; it was demonstrated that stereochemical information from the cyclopropane fragment is lost during the reaction.

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Published

2020-09-17

Issue

Vol. 56 No. 8 (2020)

Section

Short Communications