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, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 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.

Language: 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, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

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

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

Published: April 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.

Language: 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, Journal Year: 2024, Volume and Issue: 89(14), P. 10148 - 10162

Published: July 3, 2024

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

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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

Language: Английский

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