Organocatalytic Enantioselective Synthesis of Axially ChiralN,N′‐Bisindoles

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(15)

Опубликована: Фев. 7, 2023

This study establishes the first organocatalytic enantioselective synthesis of axially chiral N,N'-bisindoles via phosphoric acid-catalyzed formal (3+2) cycloadditions indole-based enaminones as novel platform molecules with 2,3-diketoesters, where de novo indole-ring formation is involved. Using this new strategy, various were synthesized in good yields and excellent enantioselectivities (up to 87 % yield 96 ee). More importantly, class exhibited some degree cytotoxicity toward cancer cells was derived into phosphine ligands high catalytic activity. provides a strategy for using asymmetric organocatalysis realize applications such scaffolds medicinal chemistry catalysis.

Язык: Английский

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Asymmetric (4+n) Cycloadditions of Indolyldimethanols for the Synthesis of Enantioenriched Indole‐Fused Rings

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(37)

Опубликована: Июнь 24, 2023

Catalytic asymmetric construction of chiral indole-fused rings has become an important issue in the chemical community because significance such scaffolds. In this work, we have accomplished first catalytic (4+2) and (4+3) cycloadditions 2,3-indolyldimethanols by using indoles 2-naphthols as suitable reaction partners under catalysis phosphoric acids, constructing enantioenriched six-membered seven-membered high yields with excellent enantioselectivities. addition, approach is used to realize enantioselective challenging tetrahydroindolocarbazole scaffolds, which are found show promising anticancer activity. More importantly, theoretical calculations pathways activation mode offer in-depth understanding class indolylmethanols. This work not only settles challenges realizing indolyldimethanols but also provides a powerful strategy for rings.

Язык: Английский

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Catalytic asymmetric (3 + 3) cycloaddition between different 2-indolylmethanols

Science China Chemistry, Год журнала: 2024, Номер 67(8), С. 2629 - 2636

Опубликована: Июнь 26, 2024

Язык: Английский

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Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality

Precision Chemistry, Год журнала: 2024, Номер 2(5), С. 208 - 220

Опубликована: Апрель 23, 2024

The catalytic asymmetric diastereodivergent synthesis of axially chiral 2-alkenylindoles was established via phosphoric acid-catalyzed addition reactions C3-unsubstituted with

Язык: Английский

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Catalytic atroposelective synthesis of indolyl quinazolinones bearing N–N/C–C diaxes

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

Язык: Английский

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Atroposelective Construction of Axially Chiral Alkene‐Indole Scaffolds via Catalytic Enantioselective Addition Reaction of 3‐Alkynyl‐2‐indolylmethanols^†

Chinese Journal of Chemistry, Год журнала: 2021, Номер 39(8), С. 2163 - 2171

Опубликована: Апрель 29, 2021

Main observation and conclusion Atroposelective construction of axially chiral alkene‐heteroaryl scaffolds is highly desired but challenging. In this work, we established an atroposelective alkene‐indole via the strategy catalytic enantioselective addition reaction 3‐alkynyl‐2‐indolylmethanols with bulky nucleophiles. strategy, α‐amido sulfones were used as competent nucleophiles phosphoric acid (CPA) acted suitable catalyst for reaction. By a new class acyclic alkene‐indoles was synthesized in overall high yields (up to 86%), excellent ( E / Z )‐selectivity (all > 95 : 5) good enantioselectivities 92 8 er). This represents first frameworks, which will add member family atropoisomeric heterocycles, especially indole compounds.

Язык: Английский

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Advances in Catalytic Asymmetric Reactions Using 2-Indolylmethanols as Platform Molecules

Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(10), С. 3351 - 3351

Опубликована: Янв. 1, 2022

Indole-based chiral heterocycles constitute a class of important heterocyclic compounds that are found in numerous natural products, pharmaceuticals, pesticide, and functional materials.The efficient highly enantioselective synthesis indole derivatives has become one the most issues organic chemistry.Due to simple reactivity traditional indoles, their involved catalytic asymmetric reactions very limited, resulting limited types constructed indole-based frameworks.To solve these challenging issues, chemists devised strategy introducing groups ring, so as obtain series functionalized derivatives, namely platform molecules, building blocks for constructing indole-related frameworks.Among them, 2-indolylmethanols which were designed on consideration introduction hydroxymethyl group C2-position ring would change reactive site ring.This molecules can act either electrophiles or nucleophiles, multi-carbon reactions.Therefore, design development have provided new derivatives.The advances using summarized, will open window designing application molecules.

Язык: Английский

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Design and Application of m‐Hydroxybenzyl Alcohols in Regioselective (3 + 3) Cycloadditions of 2‐Indolymethanols^†

Chinese Journal of Chemistry, Год журнала: 2022, Номер 41(1), С. 27 - 36

Опубликована: Сен. 16, 2022

Comprehensive Summary A new class of m ‐hydroxybenzyl alcohols has been designed as competent three‐carbon building blocks and achieved their application in 2‐indolylmethanol‐involved regioselective (3 + 3) cycloadditions under the catalysis Brønsted acids. By this appoach, a series indole‐fused six‐membered cycloadducts have synthesized overall good yields (up to 98%) with excellent regioselectivity (all >95: 5 rr), thus affording powerful method for construction rings. Moreover, catalytic asymmetric version cycloaddition preliminarily investigated, which revealed potential reaction constructing chiral rings an enantioselective manner. This work not only accomplished first design reactants, but also represents cycloadditions. In addition, provides example C3‐nucleophilic 2‐indolylmethanols, will substantially enrich chemistry 2‐indolylmethanols.

Язык: Английский

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An update on chiral phosphoric acid organocatalyzed stereoselective reactions

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(17), С. 3477 - 3502

Опубликована: Янв. 1, 2023

This review article presents an in-depth analysis of the strategies and methodologies for using chiral phosphoric acids as organocatalysts in asymmetric syntheses from recent literature.

Язык: Английский

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Design and Catalytic Asymmetric Synthesis of Furan‐Indole Compounds Bearing both Axial and Central Chirality

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(8)

Опубликована: Дек. 29, 2023

Abstract In the chemistry community, catalytic asymmetric synthesis of furan‐based compounds bearing both axial and central chirality has proven to be a significant but challenging issue owing importance difficulty in constructing such frameworks. this work, we have realized first five‐five‐membered via organocatalytic (2+4) annulation achiral furan‐indoles with 2,3‐indolyldimethanols uncommon regioselectivity. By strategy, furan‐indole were synthesized high yields excellent regio‐, diastereo‐, enantioselectivities. Moreover, theoretical calculations conducted provide an in‐depth understanding reaction pathway, activation mode, origin selectivity.

Язык: Английский

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