Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

Suzuki, Yuta; Yazaki, Ryo; Kumagai, Naoya; Shibasaki, Masakatsu

doi:10.1021/acs.orglett.6b00879

Cited by 51 publications

(10 citation statements)

References 43 publications

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“…Asymmetric Mannich‐type reaction assisted direct two‐step enolate formation followed by enantioselective C−C bond formation was achieved using low acidic amides excluding the electron‐withdrawing group at the α‐position via Mannich‐type reaction. Sun et al [121] developed facile methodology to transform amide moiety by Mannich adducts using acetate‐, propionate‐, and butyrate‐type 7‐azaindoline amides as enolate precursors with excellent stereoselectivity and ligand‐enabled diastereo‐divergency provided access to both anti / syn diastereomers (See Figure 83).…”

Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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Copper with variable oxidation states, Earth abundance was used as a tunable and multifunctional catalyst promoting organic transformations. Copper‐based catalytic materials have been effectively utilized in bioorganic chemistry, material science, and natural products synthesis. Several organic transformations involving cycloadditions, cyclizations, cross‐couplings, and condensations in one‐pot assist in the formation of multiple bonds like C−C/C−O bonds, C−C/C−N bonds, and C−N/C−S bonds. Copper has recently been explored as efficient catalytic material for the synthesis of heterocyclic amides. Heterocyclic amides are essential organic compounds are quite prevelent in the pharmaceuticals, fine chemicals and natural products. The heterocyclic amides are the key components of multivarious ace drugs and bio‐molecules like peptides and proteins, and several natural products. Therefore, heterocyclic amides are of much significance, and research focusing on the facile methods is of much interest to contemporary synthetic chemists. Different techniques have been developed using copper‐based catalysts for the synthesis of heterocyclic amdes. These heterocyclic amides are prepared by the reaction of C(sp3)−H, C(sp2)−H, C(sp)−H bonds, aldehydes, ketones, carboxylic acid, carboxylic acid‐based surrogates, and amine surrogates. N‐alkyation of amides with multifarious substrates has been the extensively investigated for the synthesis of heterocyclic amides. Finally, multicomponent domino reactions have also been investigated for the synthesis of heterocycic amides. The present review summarises various synthetic techniques for the copper catalyzed heterocyclic amides synthesis.

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Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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“…α‐Alkyl 7‐azaindoline amides can be implemented in this catalytic system for direct asymmetric Mannich‐type reactions (Scheme ) . Electron‐withdrawing groups, which enhance the acidity of the α‐proton were not essential, and the facile enolization of 7‐azaindoline amides was solely ascribed to chelating activation with the Cu I complex, followed by deprotonation with Barton's base.…”

Section: Enantioselective C−c Bond Formation By Direct Enolization Ofmentioning

confidence: 99%

Nucleophilic and Electrophilic Activation of Non‐Heteroaromatic Amides in Atom‐Economical Asymmetric Catalysis

Kumagai

Shibasaki

2016

Chemistry A European J

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Recent advances in catalytic asymmetric carbon-carbon bond-forming reactions of non-heteroaromatic amide substrates are highlighted. Among carbonyl compounds, amides have received limited attention in catalytic asymmetric transformations mainly owing to their lower reactivity. Amides are reluctant to form enolates for nucleophilic addition, and α,β-unsaturated amides exhibit diminished electrophilicity at the β-carbon. Recent advances in asymmetric catalysis rendered these amides amenable to enantioselective reactions with perfect atom economy, producing synthetically useful chiral building blocks. This Minireview summarizes recent developments in the field.

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“…[28b] a-Alkyl 7-azaindoline amides can be implemented in this catalytic system for direct asymmetricM annich-typer eactions (Scheme 11). [31] Electron-withdrawing groups,w hich enhance the acidity of the a-proton were not essential, and the facile enolization of 7-azaindolinea mides was solely ascribed to chelating activation with the Cu I complex,f ollowed by deprotonation with Barton's base. The chiral ligand of choice could toggle the diastereoselectivity,w hereby a syn selectivereaction with (R,R p )-Walphosd erivative 47 exhibited moderate stereoselectivity.…”

Section: -Azaindoline Amidesmentioning

confidence: 99%

ChemInform Abstract: Nucleophilic and Electrophilic Activation of Non‐Heteroaromatic Amides in Atom‐Economical Asymmetric Catalysis

Kumagai

Shibasaki

2016

ChemInform

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Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

Cited by 51 publications

References 43 publications

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Nucleophilic and Electrophilic Activation of Non‐Heteroaromatic Amides in Atom‐Economical Asymmetric Catalysis

ChemInform Abstract: Nucleophilic and Electrophilic Activation of Non‐Heteroaromatic Amides in Atom‐Economical Asymmetric Catalysis

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