Palladium‐Catalyzed Asymmetric Aminohydroxylation of 1,3‐Dienes

Shen, Hong‐Cheng; Wu, Yufeng; Zhang, Ying; Fan, Lian‐Feng; Han, Zhi‐Yong; Gong, Liu‐Zhu

doi:10.1002/anie.201712350

Cited by 102 publications

(48 citation statements)

References 98 publications

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“…The reaction proceeds via a cascade aminopalladation (aza-Wacker)/asymmetric allylation sequence, with the ligand 1336 chelating in a bidentate-mode throughout. 476 …”

Section: Bis(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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“…The reaction proceeds via a cascade aminopalladation (aza-Wacker)/asymmetric allylation sequence, with the ligand 1336 chelating in a bidentate-mode throughout. 476 …”

Section: Bis(oxazoline) Ligandsmentioning

confidence: 99%

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

et al. 2021

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“…In 2018, the Gong′s group reported the reaction of unactivated dienes 121 with 2‐aminophenols 122 under Pd(II) catalysis in the presence of a chiral ligand to afford enantio‐enriched benzomorpholines 123 (Scheme ) . After a first regioselective aza‐Wacker reaction, the transient palladium π‐allylic complex 124 was intramolecularly attacked by the phenolate, thus forming the benzomorpholine and releasing Pd(0) species which was in situ oxidized by the thymoquinone.…”

Section: Cyclization Through Sequential Bond Formationmentioning

confidence: 99%

Metal‐Catalyzed Cyclization: Synthesis of (Benzo)morpholines and (Benzo)[1,4]dihydrooxazines

Aubineau

Cossy

2019

Eur J Org Chem

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A review of the most recent metal-catalyzed cyclizations to access morpholines and their unsaturated derivatives, from 1993 to 2019, is reported. The review is organized accord-[a] Molecular, 7513ing to the bond(s) formed during the process. Special importance has been given to the mechanistic details of the reactions.[a] Conditions A: (MeCN) 2 PdCl 2 (10 mol-%), CH 2 Cl 2 , r.t., 5 h; Conditions B: TfOH (10 mol-%), CH 2 Cl 2 , -20°C, 5 h.

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“…6 Site-selective 1,2-addition reactions for terminal dienes or symmetrically-substituted dienes have been achieved via a sophisticated strategy using tethered oxygen/nitrogen sources, and afforded complementary regioselectivity with different metal catalysts. 7 In another example, rhodium-catalyzed amino oxygenation was achieved with chemo- and site-selectivity through a diene-tethered nitrogen group yet gave a nearly equal mixture of 1,2- and 1,4-addition products. 8 Despite these seminal developments, a three-component modular and selective amino oxygenation reaction incorporating a diverse range of 1,3-dienes remains lacking, and is greatly desired.…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids

2019

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A three-component reaction for 1,2-amino oxygenation of 1,3-dienes has been achieved using Oacyl hydroxylamines and carboxylic acids. The reaction occurs through copper-catalyzed amination of olefins followed by nucleophilic addition of carboxylic acids, offering high levels of chemo-, regio-, and site-selectivity. The method is effective for both terminal and internal 1,3dienes, including those bearing multiple, unsymmetrical substituents. The amino oxygenation conditions also exhibited remarkable selectivity toward 1,3-dienes over alkenes, good tolerance of sensitive functional groups, and reliable scalability.

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Palladium‐Catalyzed Asymmetric Aminohydroxylation of 1,3‐Dienes

Cited by 102 publications

References 98 publications

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

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

Metal‐Catalyzed Cyclization: Synthesis of (Benzo)morpholines and (Benzo)[1,4]dihydrooxazines

Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids

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