Recent advances in copper-catalyzed asymmetric propargylic substitution

Tetrahedron Chem, Год журнала: 2024, Номер 11, С. 100082 - 100082

Опубликована: Июль 3, 2024

Язык: Английский

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Copper-Catalyzed Remote Asymmetric Yne-Allylic Substitution of Yne-Allylic Esters with Anthrones

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5758 - 5763

Опубликована: Июль 1, 2024

Anthrones are key structural motifs in many natural products and pharmaceutical chemicals. However, due to its unique tricyclic aromatic structure, the synthetic space for development of chiral anthrone derivatives is largely limited. By utilizing potential copper-catalyzed remote asymmetric yne-allylic substitution reaction, we describe first example highly regio- enantioselective on various esters with anthrones under a mild reaction condition, which afforded range enantioenriched 1,3-enynes exhibiting broad functional group tolerance across 51 examples.

Язык: Английский

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Asymmetric Multicomponent Propargylations via Carbon Dioxide Shuttling and Fixation

ACS Catalysis, Год журнала: 2024, Номер 14(15), С. 11646 - 11656

Опубликована: Июль 22, 2024

Язык: Английский

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Copper-Catalyzed Dual Remote Asymmetric Vinylogous Alkynylallylic Substitution of Yne-Allylic Esters with Coumarins

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6407 - 6412

Опубликована: Июль 19, 2024

Chiral coumarins and their derivatives are ubiquitous structural motifs found in an array of biologically therapeutically active natural products drugs. Herein, a highly enantioselective dual remote copper-catalyzed vinylogous alkynylallylic substitution yne-allylic esters with has been developed. The practicality this method is exemplified by the use readily available starting materials; mild reaction conditions; excellent regio-, enantio-, stereoselectivities; very broad substrate scope (67 examples), while scalability further applications illustrated gram-scale series derivations products.

Язык: Английский

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Copper-catalyzed Larock-type cyclization/debenzylation of yne-allylic esters with aliphatic amines

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 20, 2025

Язык: Английский

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Ligand-Controlled Copper-Catalyzed Regiodivergent Sulfonylation of Yne-Vinyl Allylic Esters with Sodium Sulfinates

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 2415 - 2423

Опубликована: Янв. 27, 2025

Язык: Английский

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Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155487 - 155487

Опубликована: Янв. 1, 2025

Язык: Английский

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Copper-Catalyzed Asymmetric Cloke–Wilson Rearrangement

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 7, 2025

Herein we describe the first transition-metal-catalyzed asymmetric Cloke-Wilson rearrangement through unprecedented propargylic alkenoxylation reaction with enol as O-nucleophile. A set of new chiral PPBOX ligands was prepared to guarantee high enantioselectivity transformation. series polysubstituted dihydrofuran skeletons bearing an alkyne unit in good yield and under very mild conditions, various downstream transformations were facilely conducted access different skeletons.

Язык: Английский

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Copper-catalyzed remote asymmetric yne-allylic substitution: construction of thiazolone derivatives with adjacent chiral centers

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Herein, we report a highly diastereo- and enantioselective copper-catalyzed remote asymmetric yne-allylic substitution of esters thiazolones.

Язык: Английский

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Rh(I)/Sulfoxide‐Imine‐Olefin Complex Catalyzed Enantioselective Allylic Alkylation of 2‐Fluoromalonate: Synthesis of Chiral α‐Fluorolactone Bearing Vicinal Stereogenic Centers

Chemistry - A European Journal, Год журнала: 2024, Номер 30(68)

Опубликована: Авг. 16, 2024

Abstract Highly enantioselective Rh‐catalyzed allylic substitution of the racemic branched substrates with 2‐fluoromalonate was realized enabled by a novel chiral sulfoxide‐imine‐olefin ligand under mild reaction conditions. The utilization CuSO 4 is beneficial for improving enantioselectivity. Notably, fluoro‐containing allyl products can be employed in selective cyclic esterification to form α‐fluorolactone bearing vicinal stereogenic centers.

Язык: Английский

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