One-Pot Alkynylation/Isomerization Cascade of β-Formylated Enoates to Functionalized Ynones DOI
Rustam B. Shnigirev, Anton V. Kuzmin, Alexander Yu. Rulev

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 21, 2025

The previously unknown γ-hydroxy esters bearing both propargylic and allylic alcohol moieties were obtained from β-formylated enoates terminal alkynes. Their easy base-catalyzed isomerization into γ-keto occurred chemoselectively under metal-free conditions. In contrast to the classical two-step synthesis of carbonyl compounds alcohols involving an oxidation-reduction sequence, this protocol provides functionalized ynones in a single step readily available starting materials. Density functional theory calculations performed elucidate plausible mechanism for cascade transformations.

Language: Английский

One-Pot Alkynylation/Isomerization Cascade of β-Formylated Enoates to Functionalized Ynones DOI
Rustam B. Shnigirev, Anton V. Kuzmin, Alexander Yu. Rulev

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 21, 2025

The previously unknown γ-hydroxy esters bearing both propargylic and allylic alcohol moieties were obtained from β-formylated enoates terminal alkynes. Their easy base-catalyzed isomerization into γ-keto occurred chemoselectively under metal-free conditions. In contrast to the classical two-step synthesis of carbonyl compounds alcohols involving an oxidation-reduction sequence, this protocol provides functionalized ynones in a single step readily available starting materials. Density functional theory calculations performed elucidate plausible mechanism for cascade transformations.

Language: Английский

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