Advances in the Synthesis of Cyclopropylamines

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: March 6, 2025

Cyclopropylamines are an important subclass of substituted cyclopropanes that combine the unique electronic and steric properties with presence a donor nitrogen atom. In addition to their in diverse array biologically active compounds, cyclopropylamines utilized as synthetic intermediates, particularly ring-opening or cycloaddition reactions. Consequently, synthesis these compounds has constituted significant research topic, evidenced by abundant published methods. widely used Curtius rearrangement, classical cyclopropanation methods have been adapted integrate function (Simmons-Smith reaction, metal-catalyzed reaction diazo on olefins, Michael-initiated ring-closure reactions) advances enantioselective synthesis. More recently, specific developed for preparation aminocyclopropane moiety (Kulinkovich reactions applied amides nitriles, cyclopropenes, involving C-H functionalization, ...). The topic this review is present different cyclopropylamine derivatives, aim covering methodological best possible, highlighting scope, stereochemical aspects future trends.

Language: Английский

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Chiral Phosphoric Acid Catalyzed Asymmetric Mannich Reaction of 2-Aryl-3H-indol-3-ones with α-H Diazoacetates

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

Published: March 13, 2025

An asymmetric Mannich reaction between 2-aryl-3H-indol-3-ones and α-H diazoacetates catalyzed by chiral phosphoric acid was developed. This strategy achieves the effective synthesis of 2,2-disubstituted indolin-3-ones bearing a quaternary stereocenter containing diazo group in C2 substituent (up to >99% ee 82% yield). To demonstrate importance synthesized diversity their reactions, we successfully achieved relevant transformation reactions with (such as hydroxylation, hydrogenation, intramolecular cyclization, etc.) substituent.

Language: Английский

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Desymmetrization of Cyclohexadienones via [3+2]/[2+1] Domino Annulation: Access to Cyclopropane Fused Tricyclic Enones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 2939 - 2944

Published: April 26, 2024

Abstract A [3+2]/[2+1] domino annulation reaction of cyclohexadienones and α‐aryl vinylsulfonium salts has been reported. range cyclopropane fused tricyclic enones bearing four contiguous stereocenters were obtained as a single diastereomer in 44–93% yields. The synthetic utility was demonstrated with the gram‐scale reactions further transformations products.

Language: Английский

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KI-Catalyzed C(sp³)–H Amination and Acyloxylation of Indolin-3-ones Using Air as the Oxidant

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8162 - 8167

Published: Nov. 6, 2023

We have developed an efficient and green strategy for the synthesis of C2-amino indolin-3-ones C2-acyloxy via KI-catalyzed C(sp3)–H amination acyloxylation using air as oxidant. The reaction provides straightforward access to 2-substituted by direct functionalization at C2 position under mild conditions. Moreover, conditions enable a range complex pharmaceuticals, providing attractive products medicinal chemistry programs.

Language: Английский

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Rh(III)-Catalyzed C7-Alkylation of Isatogens with Malonic Acid Diazoesters

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 2984 - 2995

Published: Feb. 9, 2024

Rh(III)-catalyzed C7-alkylation of isatogens (indolin-3-one N-oxides) with malonic acid diazoesters has been developed. This strategy utilizes oxygen anion on the N-oxide group as a directing and successfully achieves synthesis series C7-alkylated moderate to good yields (48–86% yields). Moreover, N-oxides can not only serve simple for C7–H bond cleavage but also be deoxidized easy removal.

Language: Английский

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Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2780 - 2785

Published: Jan. 1, 2024

An unprecedented multi-component reaction with solvent participation and a novel conversion of sulfur ylides was developed via Ugi/olefination to construct pyrrolidin-5-one-2-carboxamides.

Language: Английский

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