Literature DB >> 34019404

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

Robert Connon1, Brendan Roche1, Balaji V Rokade2, Patrick J Guiry1,2.   

Abstract

The chclass="Chemical">iral <span class="Chemical">oxazoline motif is present in many ligands that have been extensively applied in a series of important <span class="Chemical">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 % ees 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.

Entities:  

Year:  2021        PMID: 34019404      PMCID: PMC8277118          DOI: 10.1021/acs.chemrev.0c00844

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  450 in total

1.  Update 1 of: C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis.

Authors:  Giovanni Desimoni; Giuseppe Faita; Karl Anker Jørgensen
Journal:  Chem Rev       Date:  2011-11-09       Impact factor: 60.622

2.  Asymmetric Induction at Remote Quaternary Centers of Cyclohexadienones by Rhodium-Catalyzed Conjugate Hydrosilylation.

Authors:  Yuki Naganawa; Mayu Kawagishi; Jun-Ichi Ito; Hisao Nishiyama
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-21       Impact factor: 15.336

3.  Asymmetric Annulation of Donor-Acceptor Cyclopropanes with Dienes.

Authors:  Hao Xu; Jiang-Lin Hu; Lijia Wang; Saihu Liao; Yong Tang
Journal:  J Am Chem Soc       Date:  2015-06-18       Impact factor: 15.419

4.  Cu-Catalyzed Enantioselective Atropisomer Synthesis via Thiolative Ring Opening of Five-Membered Cyclic Diaryliodoniums.

Authors:  Mengqing Hou; Ruixian Deng; Zhenhua Gu
Journal:  Org Lett       Date:  2018-09-07       Impact factor: 6.005

5.  Enantioselective Propargylation of Polyols and Desymmetrization of meso 1,2-Diols by Copper/Borinic Acid Dual Catalysis.

Authors:  Ren-Zhe Li; Hua Tang; Ke R Yang; Li-Qiang Wan; Xia Zhang; Jie Liu; Zhengyan Fu; Dawen Niu
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-19       Impact factor: 15.336

6.  Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: asymmetric synthesis of allyl oxindoles.

Authors:  Elizabeth C Linton; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

7.  Enantioselective iron-catalyzed azidation of β-keto esters and oxindoles.

Authors:  Qing-Hai Deng; Tim Bleith; Hubert Wadepohl; Lutz H Gade
Journal:  J Am Chem Soc       Date:  2013-04-02       Impact factor: 15.419

8.  Mg(II) -Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β-Naphthols with Dialkyl Acetylenedicarboxylates.

Authors:  Linqing Wang; Dongxu Yang; Dan Li; Pengxin Wang; Kezhou Wang; Jie Wang; Xianxing Jiang; Rui Wang
Journal:  Chemistry       Date:  2016-05-03       Impact factor: 5.236

9.  Chiral boron-bridged bisoxazoline (borabox) ligands: structures and reactivities of Pd and Cu complexes.

Authors:  Valentin Köhler; Clément Mazet; Aurélie Toussaint; Klaus Kulicke; Daniel Häussinger; Markus Neuburger; Silvia Schaffner; Stefan Kaiser; Andreas Pfaltz
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Catalytic enantioselective synthesis of tetrahydrofurans: a dynamic kinetic asymmetric [3 + 2] cycloaddition of racemic cyclopropanes and aldehydes.

Authors:  Andrew T Parsons; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2009-03-11       Impact factor: 15.419

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  6 in total

1.  Catalytic Enantioselective Synthesis of α-Difunctionalized Cyclic Sulfones.

Authors:  Eleanor Bowen; Gillian Laidlaw; Bethany C Atkinson; Timur A McArdle-Ismaguilov; Vilius Franckevičius
Journal:  J Org Chem       Date:  2022-07-08       Impact factor: 4.198

2.  Sulfur(iv)-mediated umpolung α-heterofunctionalization of 2-oxazolines.

Authors:  Qifeng Zhang; Yuchen Liang; Ruiqi Li; Ziyi Huang; Lichun Kong; Peng Du; Bo Peng
Journal:  Chem Sci       Date:  2022-04-09       Impact factor: 9.969

3.  Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF3·Et2O as the Fluorine Source and Activating Reagent.

Authors:  Hongli Chai; Xiang Zhen; Xueqing Wang; Liang Qi; Yuji Qin; Jijun Xue; Zhaoqing Xu; Hongrui Zhang; Weiwei Zhu
Journal:  ACS Omega       Date:  2022-06-01

4.  Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands.

Authors:  Sundaravel Vivek Kumar; Patrick J Guiry
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-09       Impact factor: 16.823

5.  Synthesis, resolution, and absolute configuration determination of a vicinal amino alcohol with axial chirality. Application to the synthesis of new box and pybox ligands.

Authors:  Pilar López-Ram-de-Víu; José A Gálvez; María D Díaz-de-Villegas
Journal:  Chirality       Date:  2022-05-24       Impact factor: 2.183

6.  Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines.

Authors:  Yelong Lei; Jiaxi Xu
Journal:  Beilstein J Org Chem       Date:  2022-01-05       Impact factor: 2.883

  6 in total

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