Ag(i)-catalyzed asymmetric (2+4) annulation reaction of 5-alkenyl thiazolones: synthesis of enantioenriched spiro[cyclohexenamines-thiazolones]

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(68), P. 9062 - 9065

Published: Jan. 1, 2024

We report the first metal-catalyzed (2+4) annulation of 5-alkenyl thiazolones and dicyanoalkylidenes, delivering spiro[cyclohexenamines-thiazolones] with high stereoselectivities.

Language: Английский

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Asymmetric Organocatalytic Diels–Alder Reaction of Olefinic Azlactones with Unsaturated Thiazolones: Access to Spirocyclohexenone Thiazolone Skeletons

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 15271 - 15281

Published: Oct. 10, 2024

Chiral bifunctional thiourea-catalyzed Diels-Alder reaction between olefinic azlactones and alkylidene thiazolone derivatives is reported here for the first time. The asymmetric delivers vicinal tertiary-quaternary stereocenters in spirocyclohexenone thiazolones moderate to high yields good stereochemical outcomes. protocol can be adapted a broad array of substrates. Moreover, scaled up, chiral was converted into valuable spirocyclic-1,2-amidoalcohol highlighting synthetic utility our methodology.

Language: Английский

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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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Enantioselective intramolecular tandem cyclization of o-alkynylbenzamides: generation of enantioenriched CF₃-containing spiro-isoindolinone-indoles

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2591 - 2599

Published: Jan. 1, 2024

Enantioselective intramolecular tandem cyclization of dielectrophile–dinucleophile assembled o -alkynylbenzamides provided a variety spiro-isoindolinone-indoles in low to moderate yields with good enantioselectivities.

Language: Английский

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The Construction of Novel Spirocyclic Frameworks with Cyclobutane through Rh(III)-Catalyzed [3 + 2]-Annulation between Quinoxalines and Alkynylcyclobutanols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 12912 - 12923

Published: Sept. 3, 2024

An effective synthesis strategy for the preparation of 1'

Language: Английский

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Rh(III)-Catalyzed [3 + 3]-Coupling Cyclization of 3-Hydroxyisoindolinones with Carbenoids: Rapid Access to Spirolactam Skeletons

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7728 - 7732

Published: Aug. 27, 2024

A Rh(III)-catalyzed [3 + 3]-coupling cyclization of 3-hydroxy-3-phenylisoindolinone with carbenoids has been developed. The method provides an efficient approach to access polyfunctionalized-spiro[isochromene-1,1'-isoindolin]-3'-ones good excellent reaction conversions.

Language: Английский

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Manganese(I)-Catalyzed Direct Addition of C(sp³)–H Bonds to Aryl Isocyanates

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13429 - 13437

Published: Sept. 3, 2024

The addition of C-H bonds to isocyanates catalyzed by transition metals is a highly auspicious methodology for providing synthetically and biologically important amides. However, the substrates are limited C(sp

Language: Английский

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