Palladium‐Catalyzed Asymmetric Arylation of Trifluoromethylated/Perfluoroalkylated 2‐Quinazolinones with High Enantioselectivity

Zhou, Bo; Jiang, Chunhui; Gandi, Vasudeva Rao; Lü, Yixin; Hayashi, Tamio

doi:10.1002/chem.201603105

Cited by 26 publications

(3 citation statements)

References 68 publications

(28 reference statements)

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“…Recently, Hayashi and co-workers reported a highly effective asymmetric arylation of 2-quinazolinones using a cationic palladium complex with a chiral phosphine-oxazoline ligand (S)-i-Pr-Phox (Scheme 15). 40 The procedure, in which it is necessary to add an Ag salt to generate a cationic palladium complex, showed excellent enantioselectivity (>99% ee) for all the substrates examined.…”

Section: Scheme 15 Enantioselective Arylation Of 2-quinazolinones Usimentioning

confidence: 91%

Recent Advances in the Carbon–Carbon Bond-Forming Reactions of N-Acylketimines

Asahara

2017

Synthesis

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N-Acylketimines are important synthetic building blocks used in the synthesis of a wide variety of functional amino compounds including cyclic and acyclic products. This review focuses on carbon–carbon bond-forming reactions of N-acylketimines to construct amino compounds having tetrasubstituted carbon centers.1 Introduction2 Preparation of N-Acylketimines2.1 Nucleophilic Addition of Amide Derivatives2.2 Acylation of Imine Derivatives2.3 An Aza-Wittig-Type Reaction2.4 Oxidation of Amine Precursors3 Reactions of N-Acylketimines3.1 Cyclic Ketimines3.2 Acyclic Ketimines4 Conclusions

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Section: Scheme 15 Enantioselective Arylation Of 2-quinazolinones Usimentioning

confidence: 91%

Recent Advances in the Carbon–Carbon Bond-Forming Reactions of N-Acylketimines

Asahara

2017

Synthesis

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“…[16] Hence, Lu and Hayashi introduced a new class of cyclic imines that can undergo asymmetric arylation -2-quinazolinone derivatives substituted with trifluoromethyl or perfluoroalkyl groups 61 (Scheme 29). [45] The reaction is catalyzed by the authors' previously reported catalytic system for the arylation of cyclic N-sulfonyl imines L16, [40] and generally proceeds in high yields and enantioselectivites.…”

Section: Pd-catalyzed Reactionsmentioning

confidence: 99%

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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“…In 2016, Hayashi reported a Pd-catalyzed asymmetric arylation of fluoroalkyl-substituted 2-quinazolinone derivatives (207) with arylboronic acids using (S)-iPr-PHOX (4) ligand (Scheme 57). 71 A variety of trifluoromethylated and perfluoromethylated 2-quinazoline (208) products possessing quaternary carbon stereocenters were synthesized in excellent enantioselectivities (>99% ee).…”

Section: Mono(oxazoline) Ligandsmentioning

confidence: 99%

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

et al. 2021

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The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands reported in the literature starting from 2009 until the end of 2018. The ligands are classified not by the reaction to which their metal complexes have been applied but by the nature of the denticity, chirality, and donor atoms involved. As a result, the continued development of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily monitored by the reader. In addition, the key transition states of selected asymmetric transformations will be given to illustrate the features that give rise to high levels of asymmetric induction. As a further aid to the reader, we summarize the majority of schemes with representative examples that highlight the variation in % yields and % ee s for carefully selected substrates. This Review should be of particular interest to the experts in the field but also serve as a useful starting point to new researchers in this area. It is hoped that this Review will stimulate both the development/design of new ligands and their applications in novel metal-catalyzed asymmetric transformations.

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Palladium‐Catalyzed Asymmetric Arylation of Trifluoromethylated/Perfluoroalkylated 2‐Quinazolinones with High Enantioselectivity

Cited by 26 publications

References 68 publications

Recent Advances in the Carbon–Carbon Bond-Forming Reactions of N-Acylketimines

Recent Advances in the Carbon–Carbon Bond-Forming Reactions of N-Acylketimines

Catalytic Asymmetric Arylations of Ketimines

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

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