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

被引:125
作者
Connon, Robert [1 ]
Roche, Brendan [1 ]
Rokade, Balaji, V [2 ]
Guiry, Patrick J. [1 ,2 ]
机构
[1] Univ Coll Dublin, Synth & Solid State Pharmaceut Ctr, Ctr Synth & Chem Biol, Sch Chem, Dublin 4, Ireland
[2] Univ Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, BiOrb Res Ctr, Dublin 4, Ireland
基金
爱尔兰科学基金会;
关键词
FRIEDEL-CRAFTS ALKYLATION; ALPHA-AMINO-ACIDS; HIGHLY ENANTIOSELECTIVE SYNTHESIS; DIELS-ALDER REACTION; BETA-KETO-ESTERS; 3+2 CYCLOADDITION REACTION; DEAROMATIZATION-ADDITION-REACTIONS; SYNERGISTIC CU/PD CATALYSIS; AZIDE-ALKYNE CYCLOADDITION; CARBONYL-ENE REACTIONS;
D O I
10.1021/acs.chemrev.0c00844
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 % 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.
引用
收藏
页码:6373 / 6520
页数:148
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  • [1] Water-Soluble Chiral Ruthenium(II) Phenyloxazoline Complex: Reusable and Highly Enantioselective Catalyst for Intramolecular Cyclopropanation Reactions
    Abu-Elfotoh, Abdel-Moneim
    Diem Phuong Thi Nguyen
    Chanthamath, Soda
    Phomkeona, Kesiny
    Shibatomi, Kazutaka
    Iwasa, Seiji
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) : 3435 - 3439
  • [2] Asymmetric Inter- and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex
    Abu-Elfotoh, Abdel-Moneim
    Phomkeona, Kesiny
    Shibatomi, Kazutaka
    Iwasa, Seiji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8439 - 8443
  • [3] Evaluation of Achiral Templates with Fluxional Bronsted Basic Substituents in Enantioselective Conjugate Additions
    Adachi, Shinya
    Takeda, Norihiko
    Sibi, Mukund P.
    [J]. ORGANIC LETTERS, 2014, 16 (24) : 6440 - 6443
  • [4] Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles
    Adamson, Nathan J.
    Wilbur, Katherine C. E.
    Malcolmson, Steven J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) : 2761 - 2764
  • [5] Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst
    Adamson, Nathan J.
    Hull, Ethan
    Malcolmson, Steven J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (21) : 7180 - 7183
  • [6] Two Approaches toward the Formal Total Synthesis of Oseltamivir Phosphate (Tamiflu): Catalytic Enantioselective Three-Component Reaction Strategy and L-Glutamic Acid Strategy
    Alagiri, Kaliyamoorthy
    Furutachi, Makoto
    Yamatsugu, Kenzo
    Kumagai, Naoya
    Watanabe, Takumi
    Shibasaki, Masakatsu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08) : 4019 - 4026
  • [7] Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates
    Alexy, Eric J.
    Zhang, Haiming
    Stoltz, Brian M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (32) : 10109 - 10112
  • [8] Enantioselective Photocatalytic [3+2] Cycloadditions of Aryl Cyclopropyl Ketones
    Amador, Adrian G.
    Sherbrook, Evan M.
    Yoon, Tehshik P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) : 4722 - 4725
  • [9] Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis
    Ammann, Stephen E.
    Liu, Wei
    White, M. Christina
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) : 9571 - 9575
  • [10] The Construction of Chiral Fused Azabicycles Using a Pd-Catalyzed Allylic Substitution Cascade and Asymmetric Desymmetrization Strategy
    An, Qianjin
    Liu, Delong
    Shen, Jiefeng
    Liu, Yangang
    Zhang, Wanbin
    [J]. ORGANIC LETTERS, 2017, 19 (01) : 238 - 241