Recent Progress toward the Construction of Axially Chiral Molecules Catalyzed by an N-heterocyclic Carbene

ACS Catalysis, Год журнала: 2021, Номер 11(20), С. 12520 - 12531

Опубликована: Сен. 28, 2021

Axial chirality widely exists in natural products, pharmaceutical compounds, and other functional molecules; these axially chiral compounds also find wide utility as catalysts or ligands organic synthetic chemistry. Nevertheless, whereas significant progress has been made toward the synthesis of enantioenriched molecules over past two decades, strategies involving organocatalysis have only started to emerge recently. N-heterocyclic carbene (NHC) organocatalysts recognized be powerful tools for rapid construction complex molecular architectures. However, previous works mainly focused on assembly point recently it realized that asymmetric axial could achieved by using NHCs organocatalysts. This Perspective highlights developments advances scaffolds catalyzed NHCs. The aim this is provide an overview area serve a stepping stone future investigations.

Язык: Английский

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Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(3)

Опубликована: Ноя. 2, 2023

With the rapid development of asymmetric catalysis, demand for enantioselective synthesis complex and diverse molecules with different chiral elements is increasing. Owing to unique features atropisomerism, catalytic atropisomers has attracted a considerable interest from chemical science community. In particular, introducing additional elements, such as carbon centered chirality, heteroatomic planar helical into provides an opportunity incorporate new properties axially compounds, thus expanding potential applications atropisomers. Thus, it important perform transformations synthesize bearing multiple elements. spite challenges in transformations, recent years, chemists have devised powerful strategies under organocatalysis or metal synthesizing wide range enantioenriched Therefore, become emerging field. This review summarizes progress this field indicates challenges, thereby promoting horizon.

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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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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Advances in catalytic enantioselective synthesis of chiral helicenes and helicenoids

Chem Catalysis, Год журнала: 2022, Номер 2(11), С. 3077 - 3111

Опубликована: Ноя. 1, 2022

Язык: Английский

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Catalytic Atroposelective Electrophilic Amination of Indoles

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(31)

Опубликована: Май 25, 2022

Abstract Reported here is the first catalytic atroposelective electrophilic amination of indoles, which delivers functionalized atropochiral N ‐sulfonyl‐3‐arylaminoindoles with excellent optical purity. This reaction was furnished by 1,6‐nucleophilic addition to p ‐quinone diimines. Control experiments suggest an ionic mechanism that differs from radical pathway commonly proposed for 1,6‐addition quinones. The origin selectivity investigated through computational studies. Preliminary studies show obtained 3‐aminoindoles atropisomers exhibit anticancer activities. method valuable respect enlarging toolbox amine derivatives.

Язык: Английский

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Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(3), С. 974 - 974

Опубликована: Янв. 1, 2023

a 江苏师范大学化学与材料科学学院 江苏徐州 221116

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1,3-Dipolar cycloaddition of nitrones: synthesis of multisubstituted, diverse range of heterocyclic compounds

New Journal of Chemistry, Год журнала: 2021, Номер 45(26), С. 11420 - 11456

Опубликована: Янв. 1, 2021

The 1,3-dipolar cycloaddition reaction of nitrone is one the most important methods for synthesis different sizes heterocycles which have enormous applications in natural products, biologically active molecules and pharmaceuticals.

Язык: Английский

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