Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Июнь 10, 2024

Chiral 1,2,3-triazoles are highly attractive motifs in various fields. However, achieving catalytic asymmetric click reactions of azides and alkynes for chiral triazole synthesis remains a significant challenge, mainly due to the limited systems substrate scope. Herein, we report an enantioselective azidation/click cascade reaction N-propargyl-β-ketoamides with readily available potent azido transfer reagent via copper catalysis, which affords variety up 99% yield 95% ee under mild conditions. Notably, 1,5-disubstituted triazoles that have not been accessed by previous also prepared good functional group tolerance.

Язык: Английский

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Design and Synthesis of Rigid‐Featured Tertiary Amine‐Derived C₂‐Symmetric Chiral Furan‐N,N′‐dioxide Ligands

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(42)

Опубликована: Авг. 19, 2023

Abstract To expand the chemical space of chiral N ‐oxides and furan‐containing ligands, herein we designed synthesized a new class rigid‐featured tertiary amine‐derived C 2 ‐symmetric furan‐ , N′ ‐dioxide (Fu‐2NO) ligands from optically pure l ‐prolinamides/hydroxylprolinamides in operationally simple two steps up to 57 % overall yield. The newly developed Fu‐2NO possesses pyrroloimidazolone‐based as non‐flat walls, afforded opportunity for fine‐tuning ligand electronic conformational properties by judicious choice substituent nonligating nitrogen atom. More importantly, can tolerate air moisture such that no special handling is needed their storage, be applied Ni(II)‐catalyzed asymmetric Friedel‐Crafts alkylation reaction indole.

Язык: Английский

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Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds

Catalysts, Год журнала: 2023, Номер 13(9), С. 1243 - 1243

Опубликована: Авг. 26, 2023

The functionalization of unactivated substrates through the combination copper catalysts and hypervalent iodine reagents represents a versatile tool in organic synthesis to access various classes compounds. derivatives can be used simply as oxidizing agents regenerate catalytic species or they associate starting material. In this review, special attention will paid methodologies which provide introduction nucleophiles into reagent by use suitable benziodoxol(on)es iodonium salts. Many reactions concern C- N-arylations, but may also involve formation different carbon–carbon carbon–nitrogen bonds, carbon–oxygen well carbon–halogen carbon–phosphorus bonds.

Язык: Английский

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Creation of a Chiral All-Carbon Quaternary Center Induced by CF₃ and CH₃ Substituents via Cu-Catalyzed Asymmetric Conjugate Addition

Organic Letters, Год журнала: 2024, Номер 26(25), С. 5312 - 5317

Опубликована: Июнь 13, 2024

Cu-catalyzed asymmetric construction of a chiral quaternary center bearing CH3 and CF3 groups was achieved with high to excellent enantioselectivity using our originally developed ligands. The conjugate addition Me3Al β-CF3-substituted enones unsaturated ketoesters proceeded efficiently. use gives optically active furanones in yields enantioselectivities. perfluoroalkyl-substituted enone does not seem be favorable the present reaction.

Язык: Английский

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Synthesis of Hypervalent Iodine Diazo Compounds and Their Application in Organic Synthesis

Chemistry - A European Journal, Год журнала: 2023, Номер 30(5)

Опубликована: Окт. 17, 2023

Diazomethyl-substituted iodine(III) compounds with electron-withdrawing groups (EWG) connected to diazo methyl center were a type of donor-acceptor potential reaction abilities similar ordinary compounds. Although several diazomethyl-substituted synthesized and used in the nucleophilic substitution reactions as early 1994, synthesis application new have only been reported certain extent recent years. In presence rhodium catalyst, photocatalyst, or nucleophiles, can be converted into rhodium-carbenes, diazomethyl radicals, ester radicals intermediates, which key intermediates for formation chemical bonds. The aim this review is give an overview organic synthesis.

Язык: Английский

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Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★

Acta Chimica Sinica, Год журнала: 2023, Номер 81(11), С. 1590 - 1590

Опубликована: Янв. 1, 2023

a 华东师范大学化学与分子工程学院 石油化工分子转化与反应工程全国重点实验室 上海分子治疗与新药创制工程 技术研究中心 上海市绿色化学与化工过程绿色化重点实验室 上海 200062) ( b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 200032

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Aliphatic C H azidation by Mn based mimics of α-ketoglutarate dependent enzymes

Journal of Catalysis, Год журнала: 2023, Номер 429, С. 115275 - 115275

Опубликована: Дек. 27, 2023

Язык: Английский

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Practical and regioselective halonitrooxylation of olefins to access β-halonitrates

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Авг. 20, 2024

Organic nitrates, as effective donors of the signaling molecule nitric oxide, are widely applied in pharmaceutical industry. However, practical and efficient methods for accessing organic nitrates still scarce, achieving high regiocontrol unactivated alkene difunctionalization remains challenging. Here we present a simple method highly regioselective halonitrooxylation alkenes. The approach utilizes TMSX (X: Cl, Br, or I) oxybis(aryl-λ

Язык: Английский

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Direct Selective Azidation of C(sp3)−H Groups

Tetrahedron Chem, Год журнала: 2024, Номер unknown, С. 100114 - 100114

Опубликована: Ноя. 1, 2024

Язык: Английский

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Mn-electrocatalytic oxidative C(sp³)–H azidation of 2-oxindoles and β-keto esters and azidation–cyclization of tryptamines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(2), С. 336 - 342

Опубликована: Ноя. 22, 2023

A concise electrocatalytic Mn-oxidative C(sp 3 )–H azidation approach is described. This protocol offers mild reaction conditions, broad substrate scope, and the potential for achieving enantioselective azidation.

Язык: Английский

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