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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  ∗
a   Department of Chemistry, National Institute of Technology Puducherry, Karaikal, 609609, Union Territory Puducherry, India
,
Rambabu Dandela
b   Department 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
c   Department of Chemistry, Thassim Beevi Adbul Kader College for Women, Kilakarai, Ramanathapuram, Tamilnadu, India
,
Ragupathy Dhanusuraman
a   Department of Chemistry, National Institute of Technology Puducherry, Karaikal, 609609, Union Territory Puducherry, India
› Author AffiliationsThe authors would like to thank the Department of Science and Technology, India (DST-Ref.No.: SB/FT/CS-117/2014), the Science and Engineering Research Board (SERB-Ref.No.: EEQ/2018/000574)-Ramanujan Fellowship, and the National Institute of Technology Puducherry, Karaikal, India for providing financial support. This research was supported by the SERB-DST Grant No. RJF/2020/000038. V.D. gratefully acknowledges the Ramanujan Fellowship. The author RD acknowledge ICT-IOC, Bhubaneswar for providing necessary support. Rambabu Dandela thanks DST-SERB for Ramanujan fellowship (SB/S2/RJN-075/2016), Core research grant (CRG/2018/000782) and ICT-IOC start-up grant. K.B.D. would like to acknowledge the support from the Management, Principal-Dr. S. Sumaya and the Director-Research & Industry-Institute Relations-Dr. M.S. Irfan Ahmed, Thassim Beevi Abdul Kader College for Women, Kilakarai, Ramanathapuram, Tamil Nadu, India.
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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


Publication History

Received: 15 November 2021

Accepted after revision: 12 January 2022

Accepted Manuscript online:
18 January 2022

Article published online:
08 February 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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