Enantioselective Synthesis of Spirooxindole‐pyran and furan Scaffolds via Copper‐Catalyzed Formal (3+3) and (3+2) Cycloaddition of Isatin‐derived Propargylic Esters

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(8)

Published: Dec. 12, 2024

Herein, we report a copper-catalyzed enantioselective formal (3+3) and (3+2) cycloaddition reaction of isatin-derived tertiary propargylic esters with N,N-dimethylbarbituric acid 4-hydroxycoumarins, respectively. In this process, the ester serves as both C3- C2-synthons, facilitating synthesis optically active spirooxindole-pyran furan scaffolds featuring an all-carbon quaternary stereocenter. The delivers these spirocyclic frameworks in good yields high enantioselectivities. Additionally, scalability reactions transformation chiral intermediates into valuable structures emphasize synthetic practical importance strategy.

Language: Английский

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Asymmetric Aza-Michael/Michael/Mannich Domino Reaction of 2-Aminochalcones and 5-Alkenyl-Thiazolones: Access to Enantioenriched 1,4-Sulfur-Bridged Piperidinone Skeletons

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 15, 2025

Herein, we disclose a novel organocatalytic approach for the enantioselective synthesis of 1,4-sulfur-bridged piperidinone skeletons via sequential aza-Michael/Michael/Mannich domino reaction 2-aminochalcones and 5-alkenyl-thiazolones. The one-pot catalyzed by bifunctional squaramide catalyst furnishes bridged polycyclic compounds with five contiguous stereocenters (three tertiary, two heteroquaternary) in excellent yields (up to 95%) stereochemical outcomes 99% ee up >20:1 dr). methodology offers outstanding control on regio- chemoselectivity, showcasing broad substrate compatibility. Additionally, is scalable postsynthetic transformation spirothiazolone-tetrahydroquinoline derivative further amplifies synthetic utility methodology.

Language: Английский

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Copper-catalyzed enantioselective propargylic [3 + 2] cycloaddition: access to oxygen heterocycles featuring a CF₃-substituted quaternary stereocenter

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An enantioselective Cu( i )-catalyzed propargylic [3 + 2] cycloaddition reaction for the synthesis of optically active oxygen heterocycles bearing CF 3 -substituted quaternary stereocenters has been realized.

Language: Английский

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Recent Advances in the Enantioselective Organocatalytic [4+2] Cycloadditions

Molecules, Journal Year: 2025, Volume and Issue: 30(9), P. 1978 - 1978

Published: April 29, 2025

This review covers the recent advances in asymmetric organocatalytic Diels–Alder reactions published since beginning of 2015. It describes approaches to enantioselective [4+2] cycloadditions based on application various types chiral organocatalysts.

Language: Английский

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