Relay Catalysis-Enabled Enantioselective Annulations of β,γ-Alkynyl-α-imino Esters with 1,3-Diones for the Divergent Synthesis of Chiral Oxacycles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 19, 2025

A novel protocol for the chemically divergent synthesis of chiral oxacycles has been developed using organo/metal relay catalysis. The methodology integrates a stereospecific Mannich reaction between β,γ-alkynyl-α-imino esters and 1,3-diones catalyzed by bifunctional squaramide, followed Lewis acid-catalyzed regioselective annulation reactions. By switching acid employed, we achieved pathway to construct structurally related pyran furan derivatives from common intermediate. (3+3) (3+2) products were obtained in high yields excellent stereoselectivities. Comprehensive mechanistic studies conducted establish mechanism.

Язык: Английский

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Mn(III) Catalyzed Cascade Cross-coupling / Annulation / C(O)-C Bond Insertion / Rearrangement: Access to Multi-substituted Indolenines in Water

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

Язык: Английский

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Organocatalytic Atroposelective Cross-Coupling of 2-Naphthols with Diaryliodonium Salts

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 17, 2025

Due to their modularity and conciseness, atroposelective cross-coupling is one of the most attractive approaches for synthesizing axially chiral binaphthyl molecules. While transition metal-catalyzed cross-couplings provide reliable synthetic strategies, alternative methods that accommodate a broader range substrates without pre-functionalization are highly beneficial. Here, we demonstrate using bifunctional organocatalyst (DHQD)2PHAL enables 2-naphthols diaryliodonium salts with high efficiency, yields (up 72%) excellent enantioselectivity >99% enantiomeric excess). Further transformations products highlight versatility other compounds while maintaining axial chirality.

Язык: Английский

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Dearomative Amination Cyclization of Tryptamines and Tryptophols via Enantioselective 1,6‐Addition of p‐Quinone Diimides (p‐QDIs)

Asian Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

Abstract A method utilizing p ‐quinone diimides ( ‐QDIs) as electrophilic nitrogen source to facilitate a highly enantioselective dearomative cyclization of tryptamine and tryptophol derivatives has been developed. This approach which proceeds via 1,6‐addition ‐QDIs enables the rapid efficient synthesis chiral 3‐amino‐pyrroloindoline 3‐amino‐furoindolines with excellent stereochemical control (up 99%). Development an alternate one‐pot method, coupled some synthetic transformations further elevates practical utility this strategy.

Язык: Английский

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Asymmetric Cascade Dearomatization–Cyclization Reaction of Tryptamines with β,γ-Alkynyl-α-imino Esters: Access to Hexahydropyrrolo[2,3-b]indole-Containing Tetrasubstituted α-Amino Allenoates

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10148 - 10162

Опубликована: Июль 3, 2024

An organocatalytic enantio- and diastereoselective synthesis of hexahydropyrrolo[2,3-

Язык: Английский

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Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 5, 2024

Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation Morita-Baylis-Hillman carbonates, organocatalytic dearomatization afforded an array enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34-79% yields with 61-91% ee. With Boc

Язык: Английский

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