Copper-Catalyzed Asymmetric 1,2-Arylboration of Enamines: Ac-cess to Chiral Borate-Containing 3,3’-Disubstituted Isoindolinones

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(30), С. 6085 - 6089

Опубликована: Янв. 1, 2024

An enantioselective Cu-catalyzed 1,2-arylboration reaction of N -( o -iodobenzoyl)enamines with bis(pinacolato)diboron (B 2 pin ) is developed to access chiral borate-containing 3,3′-disubstituted isoindolinones.

Язык: Английский

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Synthesis of Chiral 3H‐pyrrolo[1,2‐a]indoles via Organocatalytic Enantioselective Addition of Alkynyl Biphenyl Quinone Methides

ChemCatChem, Год журнала: 2024, Номер 16(21)

Опубликована: Июль 17, 2024

Abstract An organocatalytic enantioselective reaction utilizing α‐[4‐(4‐hydroxyphenyl)phenyl]propargyl alcohols and 3‐substituted indoles has been successfully established for the synthesis of chiral 3 H ‐pyrrolo[1,2‐ a ]indoles. Through assistance an appropriate phosphoric acid, cascade sequence is facilitated, beginning with dehydration to form alkynyl 4,4’‐biphenyl quinone methides ( 4,4’‐BQMs ). Subsequently, 1,12‐addition ]indoles these results in formation allenes, which are then protonated regenerate . Finally, intramolecular annulation occurs smoothly, leading production range high efficiency asymmetric induction.

Язык: Английский

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Construction of Nitrogen Spirocycles in a Tandem Co(III)‐catalyzed C−H Activation/Dipolar Cycloaddition Reaction

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(23), С. 4241 - 4247

Опубликована: Окт. 30, 2023

Abstract Complex spirocyclic isoindolines and pyrrolidines are formed in a tandem process involving Co(III)‐catalyzed dienylation of cyclic C‐aryl nitrones with 2,3‐butadien‐1‐ol carbonates, followed by intramolecular 1,3‐dipolar cycloaddition. The nitrone moiety serves both as directing group for the C(aryl)−H activation dipole cycloaddition step. High regioselectivity fused vs. bridged product can be obtained adjusting reaction temperature. Reactions substituted allenic substrates provide heterocycles additional stereocenters usually complete diastereoselectivity. products were readily transformed further into other complex nitrogen‐containing systems.

Язык: Английский

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Organocatalytic enantioselective (4+3) cyclization for the synthesis of spiro-fused heterocyclic compounds containing isoindolinone, oxepine and indole moieties

Chemical Communications, Год журнала: 2024, Номер 60(70), С. 9400 - 9403

Опубликована: Янв. 1, 2024

A refined strategy has been developed to control the regioselective asymmetric (4+3) cyclization of α-(3-isoindolinonyl) propargylic alcohols with 2-indolylmethanols, utilizing chiral phosphoric acid catalysis. This innovative organocatalytic yields spiro isoindolinone-oxepine-fused indoles featuring a spiro-quaternary stereocenter in high and enantioselectivities, facilitated by solvent 1,1-dichloro-1-fluoroethane additive hexafluoroisopropanol. Additionally, photophysical properties product 3k are examined, revealing bright fluorescence both solution solid state.

Язык: Английский

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Organocatalytic Asymmetric [3 + 2] Cyclization: Enantioselective Synthesis of α-Indolyl Pyrrolo[1,2-a]indole Scaffolds

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 26, 2024

A novel asymmetric [3 + 2] cyclization of α-indolyl propargylic alcohols with 3-alkyl-1H-indoles via chiral phosphoric acid catalysis has been established. This strategy allowed the synthesis pyrrolo[1,2-a]indole derivatives high yields (up to 91%) and excellent enantioselectivities 99% ee), facilitating both reaction activity enantioselectivity by using solvent CH

Язык: Английский

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