Reversible addition and elimination of alcohols by vicinal tetracarbonyl compound

Maeda, Shinya; Sudo, Atsushi; Endō, Takeshi

doi:10.1016/j.tetlet.2015.12.112

Cited by 6 publications

(1 citation statement)

References 16 publications

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“…Since then few efforts have been devoted to the synthesis of TCCs, yet even today only limited examples of symmetric TCCs have been described. The propensity of TCCs for nucleophilic addition reactions has been recognized 1 , 3 , but applications are strictly limited; 12 diazo analogs or examples with orthogonal masking of carbonyl groups are non-existent (Fig. 1c ).…”

Section: Introductionmentioning

confidence: 99%

Polyfunctionalization of vicinal carbon centers and synthesis of unsymmetric 1,2,3,4-tetracarbonyl compounds

et al. 2023

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The synthesis and characterization of organic compounds with unusual atom or functional group connectivity is one of the main driving forces in the discovery of new synthetic methods that has raised the interest of chemists for many years. Polycarbonyl compounds are such compounds wherein multiple carbonyl groups are directly juxtaposed and influence each other’s chemical reactivity. While 1,2-dicarbonyl or 1,2,3-tricarbonyl compounds are well-known in organic chemistry, the 1,2,3,4-tetracarbonyl motif remains barely explored. Herein, we report on the synthesis of such 1,2,3,4-tetracarbonyl compounds employing a synthetic strategy that involves C-nitrosation of enoldiazoacetates, while the diazo functional group remains untouched. This strategy not only leverages the synthesis of 1,2,3,4-tetracarbonyl compounds to an unprecedented level, it also accomplishes the synthesis of 1,2,3,4-tetracarbonyl compounds, wherein each carbonyl group is orthogonally masked. Combined experimental and theoretical studies provide an understanding of the reaction mechanism and rationalize the formation of such 1,2,3,4-tetracarbonyl compounds.

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Section: Introductionmentioning

confidence: 99%