Synthesis and Applications of Asymmetric Catalysis Using Chiral Ligands Containing Quinoline Motifs

Vasudevan Dhayalan; Rambabu Dandela; K. Bavya Devi; Ragupathy Dhanusuraman

doi:10.1055/a-1743-4534

SynOpen, Table of Contents

CC BY-NC-ND 4.0 · SynOpen 2022; 06(01): 31-57
DOI: 10.1055/a-1743-4534

review

Synthesis and Applications of Asymmetric Catalysis Using Chiral Ligands Containing Quinoline Motifs

Vasudevan Dhayalan ∗

^aDepartment of Chemistry, National Institute of Technology Puducherry, Karaikal, 609609, Union Territory Puducherry, India

,

Rambabu Dandela

^bDepartment of Industrial and Engineering Chemistry, Institute of Chemical Technology, Indian oil Odisha Campus, Kharagpur extension Centre, Mouza, Samantpuri, Bhubaneswar-751013, Odisha, India

,

K. Bavya Devi

^cDepartment of Chemistry, Thassim Beevi Adbul Kader College for Women, Kilakarai, Ramanathapuram, Tamilnadu, India

,

Ragupathy Dhanusuraman

^aDepartment of Chemistry, National Institute of Technology Puducherry, Karaikal, 609609, Union Territory Puducherry, India

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor Benjamin List

Abstract

In the past decade, asymmetric synthesis of chiral ligands containing quinoline motifs, a family of natural products displaying a broad range of structural diversity and their metal complexes, have become the most significant methodology for the generation of enantiomerically pure compounds of biological and pharmaceutical interest. This review provides comprehensive insight on the plethora of nitrogen-based chiral ligands containing quinoline motifs and organocatalysts used in asymmetric synthesis. However, it is confined to the synthesis of quinoline-based chiral ligands and metal complexes, and their applications in asymmetric synthesis as homogeneous and heterogeneous catalysts.

1 Introduction

2 Synthesis of Chiral Ligands Containing Quinoline Motifs

2.1 Synthesis of Schiff Base Type Chiral Ligands

2.2 Synthesis of Oxazolinyl-Type Chiral Ligands

2.3 Synthesis of Chiral N,N-Type Ligands

2.4 Synthesis of Amine-Based Chiral Ligands

2.5 Synthesis of P,N-Type Chiral Ligands

2.6 Synthesis of Chiral N-Oxide and Nitrogen Ligands

3 Homogeneous Catalytic Asymmetric Reactions

3.1 Asymmetric Carbon–Carbon Bond Formation Reactions

3.2 Asymmetric Allylic Reactions

3.3 Asymmetric Cycloadditions

3.4 Asymmetric Carbene Insertions

3.5 Asymmetric Pinacol Couplings

3.6 Asymmetric Pudovik Reactions

3.7 Asymmetric Strecker Reactions

4 Heterogeneous Catalytic Asymmetric Reactions

4.1 Asymmetric Cyclopropanation of Olefins

4.2 Asymmetric Heck Reactions

4.3 Asymmetric Hydrogenations

4.4 Asymmetric Hydroformylation of Styrene

4.5 Asymmetric Dialkoxylation of 2-Propenylphenols

4.6 Asymmetric Cascade Cyclizations

4.7 Asymmetric Allylic Alkylations

4.8 Asymmetric Alkylation of β-Keto Esters

4.9 Asymmetric C–H Bond Arylation Reactions

4.10 Intramolecular Aerobic Oxidative Amination of Alkenes

4.11 Asymmetric Oxidative Hydroboration of Alkenes

5 Conclusions

Key words

chiral ligands - catalysis - asymmetric synthesis - nitrogen heterocycles - quinoline motifs - organometallics

Full Text

References

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