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1,8-Diazabicyclo[5.4.0]undec-7-ene-Promoted Oxidation by Atmospheric Oxygen of an Allylsilane Derived from γ-Formyl-Substituted Cyclopentene

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Abstract

(1R,4R,5S-5-{[(tert-Butyldimethylsilyl)oxy]methyl}-4-(trimethylsilyl)cyclopent-2-ene-1-carbaldehyde in a toluene–DBU–O2 medium undergoes a tandem-type isomerization/oxidation transformation to form (3S,4S,5S)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-3-hydroxy-4-(trimethylsilyl)cyclopent-1-ene-1-carbaldehyde in a good yield. Possible way of formation of the product was proposed, involving the C3-oxidation of the starting allylsilane by a carbanion/enolate mechanism.

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ACKNOWLEDGMENTS

Spectral measurements and theoretical calculations were performed using the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry UFRS RAS.

Funding

The work was performed according to the State order no. AAAA-A20-120012090021-4 (АААА-А17-1170119100324) and financially supported in part by the Russian Foundation for Basic Research (project nos. 17-43-020326-а and 18-53-00011-Bel_а).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences (UFRS RAS), 450054, Ufa, Russia

    A. M. Gimazetdinov, A. Z. Al’mukhametov & M. S. Miftakhov

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  1. A. M. Gimazetdinov
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  2. A. Z. Al’mukhametov
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  3. M. S. Miftakhov
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Correspondence to M. S. Miftakhov.

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Gimazetdinov, A.M., Al’mukhametov, A.Z. & Miftakhov, M.S. 1,8-Diazabicyclo[5.4.0]undec-7-ene-Promoted Oxidation by Atmospheric Oxygen of an Allylsilane Derived from γ-Formyl-Substituted Cyclopentene. Russ J Org Chem 56, 255–260 (2020). https://doi.org/10.1134/S1070428020020128

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