Chiral Phosphoric Acid Catalyzed Asymmetric Ugi Reaction by Dynamic Kinetic Resolution of the Primary Multicomponent Adduct

Zhang, Yun; Ao, Yu‐Fei; Huang, Zhi‐Tang; Wang, De‐Xian; Wang, Mei‐Xiang; Zhu, Jieping

doi:10.1002/ange.201600751

Cited by 72 publications

(4 citation statements)

References 66 publications

(19 reference statements)

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“…In the presence of p -TsOH·H 2 O, 2-indolylethanols 1a was converted into carbocation I via dehydration, which resulted in the formation of vinyliminium species II followed by delocalized cation III . The nucleophile isonitrile 2a attacks the benzylic position of vinyliminium ion species to afford nitrilium intermediate A . Finally, nitrilium intermediate A was trapped by a water molecule that led to the desired indole-carboxamide 3a .…”

Section: Resultsmentioning

confidence: 99%

Bronsted Acid-Catalyzed Regioselective Carboxamidation of 2-Indolylmethanols with Isonitriles

et al. 2023

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A regioselective direct carboxamidation reaction of 2-indolylmethanols with readily available isocyanoesters/isocyanides has been reported in this work. The reaction was catalyzed by Bronsted acid such as p-TsOH to deliver the benzylic regioselective amides in 67–86% yield under mild conditions. The developed methodology provides alternative access to traditional metal-free carboxamidation via C–C and C–O bond formation with high atom economy. Furthermore, the developed approach was diversified to synthesize chiral indole-2-carboxamide derivatives with a moderate enantiomeric excess (61–73% ee) using an (R)-chiral phosphoric acid.

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Section: Resultsmentioning

confidence: 99%

Bronsted Acid-Catalyzed Regioselective Carboxamidation of 2-Indolylmethanols with Isonitriles

et al. 2023

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“…A significant breakthrough came in 2009 that Wang, Zhu, and coworkers employed in situ-generated chiral phosphoric acid-protonated iminium salts for the addition of α-isocyanoacetamides, furnishing chiral 5-aminooxazoles in one step 26 . Later, this chiral phosphoric acid catalytic strategy was expanded to the Ugi four-center, three-component reaction of isocyanides, anilines, and 2-formyl benzoic acid 27 , 28 . Maruoka et al developed chiral dicarboxylic acids for an enantioselective Ugi-type reaction of acyclic azomethine imines and isocyanides 29 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Ugi and Ugi-azide reactions catalyzed by anionic stereogenic-at-cobalt(III) complexes

et al. 2022

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Ugi reactions and related variations are proven to be atom and step-economic strategies for construction of highly valuable peptide-like skeletons and nitrogenous heterocycles. The development of structurally diverse range of novel catalytic systems and the discovery of new approaches to accommodate a broader scope of terminating reagents for asymmetric Ugi four-component reaction is still in high demand. Here, we report a strategy that enables enantioselective Ugi four-component and Ugi-azide reactions employing anionic stereogenic-at-cobalt(III) complexes as catalysts. The key nitrilium intermediates, generated through the nucleophilic addition of isocyanides to the chiral ion-pair which consists of stereogenic-at-cobalt(III) complexes counteranion and a protonated iminium, are trapped by either carboxylic acids or in situ-generated hydrazoic acid, delivering α-acylamino amides and α-aminotetrazoles in good to excellent enantioselectivities (up to 99:1 e.r.).

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“…[11] Particularly notable contributions have come from C. Hulme, A. Domling, and J. Zhu. [3e, 6a, d, 12] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Constrained Heterocycles Employing Two Post‐Ugi Cyclization Methods for Rapid Library Generation with In Cellulo Activity

McConnell

Kumarasamy

et al. 2017

ChemistrySelect

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Benzimidazoles and quinoxalinones are present in the core of many pharmacologically relevant compounds. Several combinatorial methods have been developed to attach ring systems to both scaffolds for derivatization at select positions. Herein, we describe the development of novel constrained heterocyclic compounds attached to the N1 position of both benzimidazole and quinoxalinone scaffolds. Utilizing robust post-Ugi cyclization methods, including the Ugi-deprotection-cyclization (UDC) methodology, allows for efficient access to a new area of chemical space. Additionally, molecular modeling and in cellulo screening was employed to therapeutically validate the compounds formed with this method.

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Chiral Phosphoric Acid Catalyzed Asymmetric Ugi Reaction by Dynamic Kinetic Resolution of the Primary Multicomponent Adduct

Cited by 72 publications

References 66 publications

Bronsted Acid-Catalyzed Regioselective Carboxamidation of 2-Indolylmethanols with Isonitriles

Bronsted Acid-Catalyzed Regioselective Carboxamidation of 2-Indolylmethanols with Isonitriles

Enantioselective Ugi and Ugi-azide reactions catalyzed by anionic stereogenic-at-cobalt(III) complexes

Synthesis of Constrained Heterocycles Employing Two Post‐Ugi Cyclization Methods for Rapid Library Generation with In Cellulo Activity

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