Biocatalytic Construction of Spiro-Oxazolidinones via Halohydrin Dehalogenase-Catalyzed Ring Expansion of Spiro-Epoxides

ACS Catalysis, Год журнала: 2024, Номер 14(14), С. 10670 - 10678

Опубликована: Июль 1, 2024

Spiro-oxazolidinones are highly valuable compounds in the fields of medicinal and organic chemistry; however, methods for synthesizing these have not been well established. Herein, we present a biocatalytic methodology construction spiro-oxazolidinones through halohydrin dehalogenase-catalyzed ring expansion spiro-epoxides. By performing screening protein engineering dehalogenases, both chiral racemic were synthesized 24–47% yields (90–98% ee) 69–98% yields, respectively. The method was also applied to efficient synthesis drug fenspiride at high substrate concentration 200 mM (44 g/L). In addition, chemo-enzymatic strategy proposed overcome limitation maximum 50% yield inherent kinetic resolution process. Moreover, large-scale representative transformations carried out provide additional evidence practicality applicability approach.

Язык: Английский

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Electrochemical Oxidative Dearomatization Strategy for Accessing Spiro[4.5]dienones and Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2200 - 2211

Опубликована: Фев. 8, 2024

Electrochemical dearomatization has been recognized as an attractive tool for the rapid construction of structurally diverse molecules. The designed methodology encompasses eco-friendly and efficient electrochemical approach to synthesizing spiro[4.5]dienones under mild reaction conditions. Furthermore, detailed mechanistic studies strongly bolster our hypothesis emphasize role HFIP in mechanism. protocol is scalable showcases a broad substrate scope with tolerance toward numerous functional groups. Henceforth, this strategy can be deployed alternative sustainable accessing spiro[4.5]dienones.

Язык: Английский

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Electrochemical dearomatization of 2-naphthols for C–O bond formation

RSC Advances, Год журнала: 2025, Номер 15(21), С. 16276 - 16280

Опубликована: Янв. 1, 2025

We reported a metal-free electrochemical oxidative C-O homocoupling of 2-naphthols, followed by subsequent alkoxylation under mild conditions. This strategy offered an eco-friendly and cost-effective approach using undivided cells. Additionally, the reaction exhibited broad tolerance to various substituted 2-naphthols diverse alcohols, affording corresponding naphthalenones in moderate good yields.

Язык: Английский

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Visible-light-induced photocatalyst-free dearomative amidation of phenol derivatives

Tetrahedron Letters, Год журнала: 2023, Номер 128, С. 154637 - 154637

Опубликована: Июнь 28, 2023

Язык: Английский

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Introduction of Molecular Complexity via the Cross‐Coupling of Lithium 1,4‐Dioxene with Aryl Bromides

Chemistry - A European Journal, Год журнала: 2024, Номер 30(61)

Опубликована: Авг. 28, 2024

Abstract The synthetic potential of substituted 1,4‐dioxenes is well recognised, although the chemistry 2‐aryl‐1,4‐dioxenes relatively unexplored. Their transition metal‐catalysed synthesis has been limited to Stille‐type cross‐coupling chemistry, typically showing long reaction times, or proceeding at high temperatures. Here we present a facile and general methodology for aryl bromides with lithium 1,4‐dioxene, affording range in generally good yields. We highlight applicability this transformation multigram scale, demonstrate versatility products by conversion dioxene units various carbonyl‐based functionalities. Additionally, concise two‐step an arylated analogue known 1,4‐dioxene‐based antifungal agent.

Язык: Английский

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Electrochemical Synthesis of Phosphorylated Azaspiro[4.5]di/trienones through Dearomative Spirocyclization

Chemical Communications, Год журнала: 2024, Номер 60(57), С. 7351 - 7354

Опубликована: Янв. 1, 2024

Cp 2 Fe-mediated electrochemical synthesis of a diverse array phosphorylated azaspiro[4.5]di/trienones has been developed, which demonstrated broad substrate scope and good diastereoselectivity.

Язык: Английский

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