Asymmetric Nucleophilic Addition to Ketones and Ketimines and Conjugate Addition Reactions

Ge, Luo; Harutyunyan, Syuzanna R.

doi:10.1002/9781119736424.ch16

Cited by 5 publications

(4 citation statements)

References 204 publications

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“…[11] Harutyunyan's book chapter focuses primarily on work using non-stabilized nucleophiles (such as Grignard or organozinc reagents). [12] Zhang's review covers Pd-catalyzed reactions, [13] while the topic of Huang's and Hayashi's review are reactions that utilize chiral diene ligands. [14] Unfortunately, because of the extensive topics covered in these reviews, a certain number of literature reports eluded inclusion.…”

Section: Introductionmentioning

confidence: 99%

“…As its title suggests, Takenaka's review on asymmetric catalytic ketimine Mannich reactions does not include arylation examples [11] . Harutyunyan's book chapter focuses primarily on work using non‐stabilized nucleophiles (such as Grignard or organozinc reagents) [12] . Zhang's review covers Pd‐catalyzed reactions, [13] while the topic of Huang's and Hayashi's review are reactions that utilize chiral diene ligands [14] …”

Section: Introductionmentioning

confidence: 99%

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Catalytic Asymmetric Arylations of Ketimines

Vlahoviček‐Kahlina,

Marijan,

Matišić

et al. 2024

Adv Synth Catal

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Arylation of ketimines is the most straightforward strategy for the construction of chiral α‐tertiary amines, important structural motifs in natural products and biologically active compounds. This comprehensive review highlights the achievements in the transition metal‐catalyzed and organocatalyzed asymmetric arylations of ketimines from the seminal report on catalytic asymmetric arylation of ketimines in 2010 till November 2023. The review is divided into three chapters: (1) Arylation of diaryl ketimines, (2) Arylation of aryl‐alkyl and aryl‐acyl ketimines, and (3) Arylation of acyl‐alkyl and dialkyl ketimines. Each chapter is further divided into transition‐metal catalyzed reactions (grouped by individual metals) and organocatalyzed reactions. Covered literature includes emphasis on the advantages of the reported methodology, its scope and limitations, and the description of the transition state (where applicable).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Arylations of Ketimines

Vlahoviček‐Kahlina,

Marijan,

Matišić

et al. 2024

Adv Synth Catal

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“…In fact, aryl and alkenyl halides and other electrophiles are often used as precursors to aryl/alkenyl metal or boron reagents . Direct use of organohalides or sulfonates in conjugate additions thus has practical advantages over existing catalytic methods such as Cu-catalyzed addition of organometal reagents of Mg, Al, Zn, etc . The organometallic reagents are sensitive to air and moisture, so they have limited tolerance to sensitive polar groups or acidic hydrogens in substrates.…”

Section: Introductionmentioning

confidence: 99%

Cobalt-Catalyzed Enantioselective Reductive Arylation, Heteroarylation, and Alkenylation of Michael Acceptors via an Elementary Mechanism of 1,4-Addition

Zhao,

Xu,

et al. 2024

J. Am. Chem. Soc.

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Cobalt complexes with chiral quinox ligands effectively promote the enantioselective conjugate addition of enones using aryl, heteroaryl, and alkenyl halides and sulfonates. Additionally, a cobalt complex with a strongly donating diphosphine, BenzP*, successfully catalyzes the asymmetric reductive arylation and alkenylation of α,βunsaturated amides. Both catalytic systems show broad scopes and tolerance of sensitive functional groups. Both reactions can be scaled up with low loadings of cobalt catalysts. Experimental results and density functional theory (DFT) calculations suggest a new mechanism of elementary 1,4-addition of aryl cobalt(I) complexes.

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“…Catalytic asymmetric arylation of aldehydes and ketones using aryl (non)metal reagents (e.g., Mg, Zn, Al, B, etc.) is one of the most useful reactions in organic synthesis . The products, carbinols, can be readily converted to other chiral building blocks such as benzylamines, amides, (thio)ethers, and azaheterocycles via benzylic substitution.…”

mentioning

confidence: 99%

Nickel-Catalyzed Enantioselective Reductive Arylation of Common Ketones

Huang,

Zhou

2024

J. Am. Chem. Soc.

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A nickel complex of chiral bisoxazolines catalyzed the stereoselective reductive arylation of ketones in high enantioselectivity. A range of common acyclic and cyclic ketones reacted without the aid of directing groups. Mechanistic studies using isolated complex of a chiral bis(oxazoline) (L)Ni(Ar)Br revealed that Mn reduction was not needed, while Lewis acidic titanium alkoxides were critical to ketone insertion.

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Asymmetric Nucleophilic Addition to Ketones and Ketimines and Conjugate Addition Reactions

Cited by 5 publications

References 204 publications

Catalytic Asymmetric Arylations of Ketimines

Catalytic Asymmetric Arylations of Ketimines

Cobalt-Catalyzed Enantioselective Reductive Arylation, Heteroarylation, and Alkenylation of Michael Acceptors via an Elementary Mechanism of 1,4-Addition

Nickel-Catalyzed Enantioselective Reductive Arylation of Common Ketones

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