Synthesis and ethylene-promoted metathesis of adducts of tandem [4+2]/[4+2] cycloaddition between bis-furyl dienes and maleic acid derivatives

During this work, a series of 1,4:5,8-diepoxynaphthalenes, annellated with various carbo- and heterocycles, was synthesized based on the tandem intermolecular/intramolecular [4+2] cycloaddition of bis-furyl dienes with moderately to highly reactive cyclic dienophiles (maleic anhydride and maleinimides). The stereochemistry of the resulting adducts was established using 2D NMR and X-ray structural analysis, which showed that both successive Diels-Alder reactions led to single diastereoisomers of the target cycloadducts corresponding to the exo-transition state. The resulting hexacyclic compounds represent original polyfunctional synthons suitable for subsequent transformations, which has been demonstrated by the example of the ethylene-promoted ROCM reaction under new types of second-generation Hoveyda-Grubbs catalysts comprising a coordination N → Ru bond in a six-membered ring. As a result, the metathesis products, unsaturated 4,7-epoxyisobenzofurans, were obtained in satisfactory yields. This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Publisher
Royal Society of Chemistry
Number of issue
7
Language
English
Pages
3400-3407
Status
Published
Volume
45
Year
2021
Organizations
  • 1 Organic Chemistry Department, Faculty of Science, Peoples' Friendship University of Russia, RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 2 N. D. Zelinsky Institute of Organic Chemistry of RAS, 47 Leninsky Prospect, Moscow, 119991, Russian Federation
Keywords
Aliphatic compounds; Cycloaddition; Ethylene; Nuclear magnetic resonance spectroscopy; Diastereoisomers; Diels-Alder reaction; Heterocycles; Polyfunctional; Reaction under; Second generation hoveyda-grubbs catalysts; Six-membered rings; Transition state; Coordination reactions
Date of creation
20.04.2021
Date of change
20.04.2021
Short link
https://repository.rudn.ru/en/records/article/record/72112/
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