Journal ArticleDOI
Chiral N,N′-dioxide ligands: synthesis, coordination chemistry and asymmetric catalysis
TLDR
In this paper, a class of conformationally flexible ligands composed of a tertiary amino oxide-amide backbone and a straight-chain alkyl spacer was developed, which act as neutral tetradentate ligands to bind a wide variety of metal ions.Abstract:
A class of conformationally flexible ligands composed of a tertiary amino oxide–amide backbone and a straight-chain alkyl spacer was developed. These C2-symmetric chiral N,N′-dioxide ligands could be straightforwardly synthesized from readily available amino acids and amines. They act as neutral tetradentate ligands to bind a wide variety of metal ions. Non-planar cis-α M(N,N′-dioxide) complexes enable an intriguing and easily fine-tuned chiral platform for a number of asymmetric reactions. Privileged N,N′-dioxide ligands frequently show wide substrate generality and exceptional levels of stereocontrol for a specific catalytic reaction. We describe approaches to the ligand design and synthesis, structure and bonding in coordination complexes, and the recent developments in asymmetric catalysis.read more
Citations
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Catalytic asymmetric synthesis of spirooxindoles: recent developments
Guang-Jian Mei,Feng Shi +1 more
TL;DR: This feature article outlines the recent progress in the catalytic asymmetric synthesis of spirooxindoles, including the contributions of the group of scientists from the University of California, Berkeley.
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Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral N,N′-Dioxide–Metal Complexes
TL;DR: Recent studies on asymmetric cycloadditions between various dienophiles and dienes, dipoles and dipolarophiles, and cascade cyclizations catalyzed by chiral N,N'-dioxide-metal complexes reveal the importance of tunability and compatibility of the ligands and metal precursors for achieving high stereoinduction and activity.
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Chiral Amino Acids‐Derived Catalysts and Ligands
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Asymmetric Dearomatization of Indoles through a Michael/Friedel–Crafts‐Type Cascade To Construct Polycyclic Spiroindolines
TL;DR: A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N'-dioxide/Mg(II) catalyst.
Journal ArticleDOI
Regio- and Enantioselective Aza-Diels–Alder Reactions of 3-Vinylindoles: A Concise Synthesis of the Antimalarial Spiroindolone NITD609
TL;DR: An asymmetric aza-Diels-Alder reaction of 3-vinylindoles with isatin-derived ketimines has been developed and a series of spiroindolone derivatives were obtained in good to excellent yields with excellent enantioselectivity.
References
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Journal ArticleDOI
Privileged Chiral Catalysts
Tehshik P. Yoon,Eric N. Jacobsen +1 more
TL;DR: Drawing inspiration from natural catalysts, chemists have developed a variety of synthetic small-molecule catalysts that can achieve levels of selectivity approaching, and in some cases matching, those observed in enzymatic reactions.
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Chiral Diphosphine and Monodentate Phosphorus Ligands on a Spiro Scaffold for Transition-Metal-Catalyzed Asymmetric Reactions
Jian-Hua Xie,Qi-Lin Zhou +1 more
TL;DR: The design and synthesis of a new family of chiral spiro phosphorus ligand including spiro diphosphines and spiro monodentate phosphorus ligands with 1,1'-spirobiindane and 9,9-spirobifluorene backbone and their applications in transition-metal-catalyzed asymmetric hydrogenation and carbon-carbon bond formation reactions are outlined.
Journal ArticleDOI
Chiral N,N′-Dioxides: New Ligands and Organocatalysts for Catalytic Asymmetric Reactions
TL;DR: The design of a new family of C(2)-symmetric N,N'-dioxides from readily available chiral amino acids is outlined, and the application of these chiral amine N-oxides as useful metal ligands and organocatalysts for asymmetric reactions are discussed.
Journal ArticleDOI
Update 1 of: C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis.
TL;DR: update 1 of: C2-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis Giovanni Desimoni,* Giuseppe Faita, and Karl Anker Jørgensen