REACTIVITY OF ALICYCLIC 1,5,9-TRIKETONES TOWARD FIVE-, SIX-, AND SEVEN-MEMBERED RINGS IN ACIDIC MEDIUM. STEREOCHEMISTRY OF INTRAMOLECULAR CYCLIZATION PRODUCTS

Authors

  • Таисия И. Акимова School of Natural Sciences, Far Eastern Federal University, 10, Build. L Universitetskiy Ave., Ayaks Village, Russky Island, Vladivostok 690922, Russia
  • Ольга А. Солдаткина School of Natural Sciences, Far Eastern Federal University, 10, Build. L Universitetskiy Ave., Ayaks Village, Russky Island, Vladivostok 690922, Russia
  • Андрей В. Герасименко Institute of Chemistry, Far East Branch of the Russian Academy of Sciences, 159 100-letiya Vladivostoka Ave., Vladivostok 690022, Russia
  • Вячеслав Г. Савченко School of Natural Sciences, Far Eastern Federal University, 10, Build. L Universitetskiy Ave., Ayaks Village, Russky Island, Vladivostok 690922, Russia
  • Алевтина А. Капустина School of Natural Sciences, Far Eastern Federal University, 10, Build. L Universitetskiy Ave., Ayaks Village, Russky Island, Vladivostok 690922, Russia

DOI:

https://doi.org/10.1007/6379

Keywords:

alicyclic 1, 5, 9-triketones, diastereomers, hemiacetals, diastereoselectivity, intramolecular cyclization.

Abstract

Among nine alicyclic 1,5,9-triketones with differently fused 5-, 6-, and 7-membered rings in the molecule, existing as mixtures of 3–6 diastereomers, only those containing at least two 6-membered rings were capable of intramolecular cyclization in acidic medium (HCl, EtOH). The diastereomer mixture underwent stereoselective transformation, giving one major cyclization product. The relative configuration of chiral centers in cyclization products obtained under acidic or basic conditions was compared by X-ray crystallography. The differences were caused by divergent stereochemical outcome at the first stage of cyclization.

 

Author Biographies

Таисия И. Акимова, School of Natural Sciences, Far Eastern Federal University, 10, Build. L Universitetskiy Ave., Ayaks Village, Russky Island, Vladivostok 690922, Russia

Кафедра органической химии, профессор

Ольга А. Солдаткина, School of Natural Sciences, Far Eastern Federal University, 10, Build. L Universitetskiy Ave., Ayaks Village, Russky Island, Vladivostok 690922, Russia

Кафедра органической химии, магистрант

Андрей В. Герасименко, Institute of Chemistry, Far East Branch of the Russian Academy of Sciences, 159 100-letiya Vladivostoka Ave., Vladivostok 690022, Russia

Заведующий лабораторией, к.х.н.

Вячеслав Г. Савченко, School of Natural Sciences, Far Eastern Federal University, 10, Build. L Universitetskiy Ave., Ayaks Village, Russky Island, Vladivostok 690922, Russia

Завдующий лабораторией молекулярного анализа

Алевтина А. Капустина, School of Natural Sciences, Far Eastern Federal University, 10, Build. L Universitetskiy Ave., Ayaks Village, Russky Island, Vladivostok 690922, Russia

Кафедра неорганической и элементорганической химии, доцент

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Published

2021-11-26

Issue

Vol. 57 No. 11 (2021)

Section

Original Papers