Copper-Catalyzed Asymmetric Yne-Allylic Substitution Using Electron-Rich Arenes

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(4), P. 2746 - 2757

Published: Feb. 7, 2024

Remote stereocontrol in transition-metal catalysis is a challenging but interesting research topic. In this work, we achieved copper-catalyzed asymmetric yne-allylic substitution using electron-rich arenes and acyclic carbonates through remote enantioselectivity control. The reaction delivers variety of enantioenriched products that contain diverse set valuable moieties, such as conjugated enynes, indoles, indolizines, allenes, dihydrofurans, which are widely used organic synthesis act key units bioactive molecules natural products. synthetic value protocol has been demonstrated series further transformations, mechanistic studies have conducted to gain more insight into the reaction.

Language: Английский

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Asymmetric copper-catalyzed alkynylallylic monofluoroalkylations with fluorinated malonates

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(31), P. 4210 - 4213

Published: Jan. 1, 2024

The unprecedented copper-catalyzed asymmetric alkynylallylic monofluoroalkylation reaction is described

Language: Английский

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Recent advances in copper-catalyzed asymmetric propargylic substitution

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100082 - 100082

Published: July 3, 2024

Language: Английский

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Enantioselective Copper-Catalyzed Dearomative Spiroannulation of β-Naphthols or Indoles with Yne-Allylic Esters

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(12), P. 9254 - 9264

Published: June 3, 2024

Catalytic asymmetric dearomatization reactions of α-unsubstituted β-naphthols are very challenging due to the high energy barrier resulting from loss aromaticity. Herein, we describe an example enantioselective catalytic dearomative spiroannulation with yne-allylic esters. The success this reaction relied on copper-catalyzed remote strategy using esters as bis-electrophilic reagents. This transformation features mild conditions, broad functional group tolerance, and extensive substrate scope, thereby facilitating efficient construction array enantioenriched naphthalene-2-one spiroindolenine derivatives. Experimental studies density theory calculations establish pathway origin stereoselectivity.

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5758 - 5763

Published: July 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.

Language: Английский

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Asymmetric Multicomponent Propargylations via Carbon Dioxide Shuttling and Fixation

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11646 - 11656

Published: July 22, 2024

Language: Английский

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Copper-Catalyzed [4+1] and [4+2] Reactions through Tandem ­Remote Propargylation/Cyclization/Isomerization with an Amine or a Hydrazine

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: March 25, 2024

Abstract Two novel copper-catalyzed cyclization reactions involving a remote propargylic substitution/cyclization/isomerization cascade are disclosed. Derivatives of the seldomly studied heterocycles thieno[2,3-c]pyrrole and thieno[2,3-d]pyridazine conveniently synthesized in moderate to good yields from primary amines or arylhydrazines through [4+1] [4+2] reactions, respectively. Preliminary mechanistic experiments corroborated occurrence designed reactions.

Language: Английский

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Copper-catalyzed asymmetric [4 + 1] annulation of yne-allylic esters with pyrazolones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110114 - 110114

Published: June 1, 2024

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6407 - 6412

Published: July 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.

Language: Английский

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Copper-catalyzed amine-mediated yne-propargylic substitution

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3946 - 3951

Published: Jan. 1, 2024

A copper-catalyzed yne-propargylic substitution using amines as nucleophiles has been achieved for the first time, affording a variety of having diyne moieties, which are important pharmacophores in many bioactive molecules.

Language: Английский

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