Application of New Efficient Hoveyda-Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles

The ring rearrangement metathesis (RRM) of a trans-cis diastereomer mixture of methyl 3-allyl-3a,6-epoxyisoindole-7-carboxylates derived from cheap, accessible and renewable furan-based precursors in the presence of a new class of Hoveyda-Grubbs-type catalysts, comprising an N→Ru coordinate bond in a six-membered ring, results in the difficult-to-obtain natural product-like cyclopenta[b]furo[2,3-c]pyrroles. In this process, only one diastereomer with a trans-arrangement of the 3-allyl fragment relative to the 3a,6-epoxy bridge enters into the rearrangement, while the cis-isomers polymerize almost completely under the same conditions. The tested catalysts are active in the temperature range from 60 to 120 °C at a concentration of 0.5 mol % and provide better yields of the target tricycles compared to the most popular commercially available second-generation Hoveyda-Grubbs catalyst. The diastereoselectivity of the intramolecular Diels-Alder reaction furan (IMDAF) reaction between starting 1-(furan-2-yl)but-3-en-1-amines and maleic anhydride, leading to 3a,6-epoxyisoindole-7-carboxylates, was studied as well.

Авторы
Antonova A.S. 1 , Vinokurova M.A. 1 , Kumandin P.A. 1 , Merkulova N.L. 1 , Sinelshchikova A.A.2 , Grigoriev M.S.2 , Novikov R.A. 3 , Kouznetsov V.V.4 , Polyanskii K.B. 1 , Zubkov F.I. 1
Журнал
Издательство
MDPI AG
Номер выпуска
22
Язык
Английский
Статус
Опубликовано
Том
25
Год
2020
Организации
  • 1 Organic Chemistry Department, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya St.Moscow 117198, Russian Federation
  • 2 A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31 ,bld. 4Moscow 119071, Russian Federation
  • 3 V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov Street ,32Moscow 119991, Russian Federation
  • 4 Laboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguara, Km 2 vía refugio, Colombia
Ключевые слова
3-allyl-3a,6-epoxyisoindoles; cyclopenta[b]furo[2,3-c]pyrroles; furan; Hoveyda–Grubbs catalysts; IMDAF reaction; nitrogen–ruthenium coordinate bond; ring-rearrangement metathesis
Дата создания
20.04.2021
Дата изменения
20.04.2021
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/72558/
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