Vinyl and Alkynyl Substituted Heterocycles as Privileged Scaffolds in Transition Metal Promoted Stereoselective Synthesis

Ghorai, Debasish; Tóth, Balázs L.; Lanzi, Matteo; Kleij, Arjan W.

doi:10.1021/acs.accounts.3c00760

Cited by 8 publications

(1 citation statement)

References 55 publications

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“…1 Therefore, over the past few decades, the installation of CF 3 groups in organic molecules has been a popular topic of discussion. 2 The five-membered cyclic carbonates are not only considered crucial components for synthesizing high-quality chemicals, potent bioactive compounds, pharmaceuticals, and polymers, 3–6 but they have also been identified in various natural products and promising drugs. 7 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF₃-containing five-membered cyclic carbonates

Mao,

Wang,

Zhong

et al. 2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF₃-containing five-membered cyclic carbonates

Mao,

Wang,

Zhong

et al. 2024

Org. Chem. Front.

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Chemo‐, Regio‐ and Stereoselective Preparation of (Z)‐2‐Butene‐1,4‐Diol Monoesters via Pd‐Catalyzed Decarboxylative Acyloxylation

Cheng,

Zhao,

Zhang

et al. 2024

Chemistry A European J

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(Z)‐alkenes are useful synthons but thermodynamically less stable than their (E)‐isomers and typically more difficult to prepare. The synthesis of 1,4‐hetero‐bifunctionalized (Z)‐alkenes is particularly challenging due to the inherent regio‐ and stereoselectivity issues. Herein we demonstrate a general, chemoselective and direct synthesis of (Z)‐2‐butene‐1,4‐diol monoesters. The protocol operates within a Pd‐catalyzed decarboxylative acyloxylation regime involving vinyl ethylene carbonates (VECs) and various carboxylic acids as the reaction partners under mild and operationally attractive conditions. The newly developed process allows access to a structurally diverse pool of (Z)‐2‐butene‐1,4‐diol monoesters in good yields and with excellent regio‐ and stereoselectivity. Various synthetic transformations of the obtained (Z)‐2‐butene‐1,4‐diol monoesters demonstrate how these synthons are of great use to rapidly diversify the portfolio of these formal desymmetrized (Z)‐alkenes.

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Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation

Zhang,

Liang,

Zhang

et al. 2024

Org. Lett.

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A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process of C–C bond activation and intermolecular allylic substitution was well-organized. The key for this transformation is the in situ generated hydrolysis product of cyclopropenone, which triggered a new reaction with vinylethylene carbonates. The reaction mechanism was investigated, demonstrating the high stereoselectivity and excellent atomic economy in this process.

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Vinyl and Alkynyl Substituted Heterocycles as Privileged Scaffolds in Transition Metal Promoted Stereoselective Synthesis

Abstract: A detailed mechanistic analysis of a ternary catalyst was achieved for a photoredox/transition metal catalyzed stereoselective formation of quaternary carbon centers.

Cited by 8 publications

References 55 publications

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF₃-containing five-membered cyclic carbonates

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF₃-containing five-membered cyclic carbonates

Chemo‐, Regio‐ and Stereoselective Preparation of (Z)‐2‐Butene‐1,4‐Diol Monoesters via Pd‐Catalyzed Decarboxylative Acyloxylation

Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation

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Vinyl and Alkynyl Substituted Heterocycles as Privileged Scaffolds in Transition Metal Promoted Stereoselective Synthesis

Abstract: A detailed mechanistic analysis of a ternary catalyst was achieved for a photoredox/transition metal catalyzed stereoselective formation of quaternary carbon centers.

Cited by 8 publications

References 55 publications

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF3-containing five-membered cyclic carbonates

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF3-containing five-membered cyclic carbonates

Chemo‐, Regio‐ and Stereoselective Preparation of (Z)‐2‐Butene‐1,4‐Diol Monoesters via Pd‐Catalyzed Decarboxylative Acyloxylation

Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation

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Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF₃-containing five-membered cyclic carbonates

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF₃-containing five-membered cyclic carbonates