Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor–Acceptor Cyclopropanes with Indoline-2-Thiones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 20, 2025

Lewis acid-enabled reactions of donor-acceptor cyclopropanes (DACs) with indoline-2-thiones are reported. The reaction exhibits tunable annulation depending on the acid and substituent at N1 indoline-2-thiones. With AlCl3 as 1-isopropylindoline-2-thiones reactants, a direct ring opening DACs, followed by intramolecular nucleophilic addition/dehydration takes place leading to formation dihydro-2H-thiepino[2,3-b]indoles in moderate good yields. Using Yb(OTf)3 promoter 1-unsubstituted (3 + 2) cycloaddition DACs accompanied sulfur rearrangement give 3-indolyl-4,5-dihydrothiophenes In addition, synthetic transformation 3-indolyl-4,5-dihydrothiophene sulfone indole-based axially chiral scaffolds further extends utility structural complexity.

Language: Английский

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Pentafluorophenol (C6F5OH) catalyzed Regioselective annulation for the synthesis of tetracyclic Dihydrochromeno indoles

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155660 - 155660

Published: May 1, 2025

Language: Английский

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Organocatalytic Asymmetric [4 + 4] Annulation Reaction of Ynones with Unsaturated Pyrazolones: Synthesis of Eight-Membered Ether-Embedded 4,5-Fused Pyrazoles

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

Published: May 20, 2025

An aminocatalytic asymmetric (4 + 4) annulation of ynones and unsaturated pyrazolones is reported. This study the first to describe an enantioselective synthesis eight-membered ether-embedded 4,5-fused pyrazoles. The scope reaction broad, cyclic ether-containing pyrazole products were isolated in moderate good yields with high enantioselectivities.

Language: Английский

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Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4812 - 4819

Published: Jan. 1, 2024

A catalytic asymmetric formal (2 + 3) cycloaddition of methyl-substituted 2-indolylmethanols was established, which delivered various chiral pyrroloindoles in overall high yields with excellent diastereoselectivities and good enantioselectivities.

Language: Английский

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Highly Enantioselective Construction of Chiral Eight-Membered Cyclic Ethers through Tandem Cyclization of Ynones and Dicarbonyl Compounds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16736 - 16749

Published: Oct. 30, 2024

The enantioselective synthesis of eight-membered cyclic ether has always been a challenge in organic synthesis. Herein, we reported highly tandem cyclization reaction alkyne ketone and dioxypyridines mediated by chiral bifunctional catalysts. This generates two adjacent stereocenters using an atomeconomic manner, providing simple effective method for the one-step ethers.

Language: Английский

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Bro̷nsted Acid-Catalyzed Regioselective [5 + 1] Annulation for the Synthesis of Indole-Fused Dihydrochromanes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16791 - 16803

Published: Nov. 3, 2024

A Bro̷nsted acid-catalyzed [5 + 1] annulation of 2-(1

Language: Английский

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Biaxially chiral compounds: research and development of synthesis

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

To date, two asymmetric catalytic methods have been established for the synthesis of biaxially chiral molecules: transition-metal-catalysis and organocatalysis.

Language: Английский

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Enantioselective Synthesis of Nonfused Eight-Membered O-Heterocycles by Sequential Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 27(1), P. 340 - 345

Published: Dec. 30, 2024

This work describes a chiral bifunctional squaramide/DBU sequential catalytic strategy for the enantioselective synthesis of nonfused eight-membered O-heterocycles through asymmetric addition ynones to β,γ-unsaturated α-ketoesters followed by regio- and diastereoselective cyclization adduct intermediates. Mechanistic experiments revealed that an isomerization process should be involved in ring formation step, origin high regioselectivity diastereoselectivity has also been elucidated DFT calculations.

Language: Английский

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Asymmetric Organocatalytic Benzylation of Morita–Baylis–Hillman Carbonates with 2,4-Dinitrotoluene Derivatives

Synthesis, Journal Year: 2024, Volume and Issue: 56(20), P. 3181 - 3190

Published: July 5, 2024

Abstract The organocatalytic asymmetric benzylation of Morita–Baylis–Hillman (MBH) carbonates with 2,4-dinitrotoluene derivatives as nucleophiles is described. developed reaction provides a straightforward access to functionalized biological and synthetic relevance. Highly products have been chemoselectively efficiently obtained in good high yields (up 84%) excellent stereoselectivity >20:1 dr, >99 ee).

Language: Английский

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B(C₆F₅)₃-Catalyzed Multicomponent Reactions of 2,3-Diketoesters, Amines, Allenes, and Nucleophiles: Synthesis of 2α-Functionalized Pyrroles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12286 - 12297

Published: Aug. 15, 2024

An efficient B(C6F5)3-catalyzed multicomponent reaction of 2,3-diketoesters, amines, allenes, and nucleophiles was reported, which afforded 2α-functionalized pyrroles in moderate to good yields. The features low catalyst loading, usage a small amount solvent, high atom economy, tunable installation diverse functional groups at 2α-position, water being formed as the byproduct. This is first that combines vicinal tricarbonyl compounds with allenes.

Language: Английский

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