Enantioselective merged gold/organocatalysis

Pegu, Chayanika; Paroi, Bidisha; Patil, Nitin T.

doi:10.1039/d4cc00114a

Cited by 4 publications

(2 citation statements)

References 122 publications

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“…The first strategy introduced propargylic alcohols via oxidative αetherification with excellent stereocontrol. The alkyne handle was then coupled to an electron-rich aryl ring by gold(I)catalyzed intramolecular hydroarylation [9,10] to furnish 1,3,4substituted α-quaternary isochromanes. The second strategy is based on a Friedel-Crafts type intramolecular allylic alkylation [11] as the key reaction.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of α‐Quaternary Isochromanes by Oxidative Aminocatalysis and Gold Catalysis

Waser,

Faghtmann,

Gil‐Ordóñez

et al. 2024

Chemistry A European J

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A novel strategy that combines oxidative aminocatalysis and gold catalysis allows the preparation of chiral α‐quaternary isochromanes, a motif that is prevalent in natural products and synthetic bioactive compounds. In the first step, α‐branched aldehydes and propargylic alcohols are transformed into α‐quaternary ethers with excellent optical purities (>90% ee) via oxidative umpolung with DDQ and an amino acid‐derived primary amine catalyst. Subsequent gold(I)‐catalyzed intramolecular hydroarylation affords the isochromane products with retention of the quaternary stereocenter. A second approach explores the use of allylic alcohols as reaction partners for the oxidative coupling to furnish α‐quaternary ethers with generally lower enantiopurities. Stereoretentive cyclization to isochromane products is achieved via intramolecular Friedel‐Crafts type alkylation with allylic acetates as a reactive handle. A number of synthetic elaborations and a biological study on these α‐quaternary isochromanes highlight the potential applicability of the presented method.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of α‐Quaternary Isochromanes by Oxidative Aminocatalysis and Gold Catalysis

Waser,

Faghtmann,

Gil‐Ordóñez

et al. 2024

Chemistry A European J

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“…On the other hand, gold(I) complexes, recognized as strong π-acids, exhibit high affinity to C–C multiple bonds and feature kinetically labile carbon–metal bonds . This property makes them potent carbophilic catalysts for alkyne activation, driving diverse transformations. , For instance, gold complexes have been utilized to convert yne–enones into diverse furan derivatives and allenes (Scheme B), typically through furan-based metal 1,3-dipoles, o -quinodimethanes ( o QDMs), or allenyl-metal species. , …”

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confidence: 99%

Cooperative Gold(I)/DMAP Catalysis Enabled (2 + 3) Cycloadditions of Yne–Enones with Oxindole-Derived MBH Carbonates

Zhao,

Yao,

et al. 2024

Org. Lett.

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A cooperative gold(I)/DMAP system catalyzes the (2 + 3) cycloadditions of yne−enones with oxindole-derived Morita−Baylis−Hillman (MBH) carbonates, yielding diverse bispiro-cyclopentene oxindole products. The mild, scalable protocol demonstrates broad substrate scope and excellent chemo-and diastereoselectivity. Mechanistic study reveals pivotal roles of both catalysts in the unique (2 + 3) cycloaddition. This strategy showcases superiority in achieving transformation with unique chemoselectivity and excellent diastereoselectivity, unattainable through traditional monocatalytic methodologies.

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Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels–Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles

León Rojas,

Chong,

Kyne

et al. 2024

Org. Lett.

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Enantioselective merged gold/organocatalysis

Abstract: Gold complexes, relying on their unique carbophilic nature, have evolved as efficient catalysts to achieve various functionalization reactions of C─C multiple bonds. However, the realization of enantioselective transformations via gold...

Cited by 4 publications

References 122 publications

Enantioselective Synthesis of α‐Quaternary Isochromanes by Oxidative Aminocatalysis and Gold Catalysis

Enantioselective Synthesis of α‐Quaternary Isochromanes by Oxidative Aminocatalysis and Gold Catalysis

Cooperative Gold(I)/DMAP Catalysis Enabled (2 + 3) Cycloadditions of Yne–Enones with Oxindole-Derived MBH Carbonates

Enantioselective and Regiodivergent Gold and Chiral Brønsted Acid Catalyzed Cycloisomerization/Diels–Alder Reaction of 1,10-Dien-4-yn-3-yl Acetates: Synthesis of Norbornene-Embedded Tricarbocycles

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