The preparation and resolution of novel axially chiral pyrazine‐containing P,N ligands for asymmetric catalysis and their application in palladium‐catalysed allylic substitution

2021 ◽  
Author(s):  
Patrick Jerome Guiry ◽  
Sarah Kelly ◽  
Richard Goddard
Keyword(s):  
Asymmetric Catalysis ◽  
Allylic Substitution ◽  
Axially Chiral

scholarly journals Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

2021 ◽  
Vol 17 ◽  
pp. 2729-2764
Author(s):  
Alemayehu Gashaw Woldegiorgis ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Catalysis ◽  
Medicinal Chemistry ◽  
High Efficiency ◽  
Biologically Active ◽  
Chiral Compounds ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Axially Chiral ◽  
Acid Catalyzed

In recent years, the synthesis of axially chiral compounds has received considerable attention due to their extensive application as biologically active compounds in medicinal chemistry and as chiral ligands in asymmetric catalysis. Chiral phosphoric acids are recognized as efficient organocatalysts for a variety of enantioselective transformations. In this review, we summarize the recent development of chiral phosphoric acid-catalyzed synthesis of a wide range of axially chiral biaryls, heterobiaryls, vinylarenes, N-arylamines, spiranes, and allenes with high efficiency and excellent stereoselectivity.

Synthesis and Optical Resolution of Aminophosphines with Axially Chiral C(aryl)−N(amine) Bonds for Use as Ligands in Asymmetric Catalysis

2006 ◽  
Vol 71 (19) ◽  
pp. 7346-7353 ◽  
Author(s):  
Takashi Mino ◽  
Youichi Tanaka ◽  
Youtaro Hattori ◽  
Toshihiro Yabusaki ◽  
Hiroaki Saotome ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Optical Resolution ◽  
Axially Chiral

Enantiomerically pure 1-(2-methoxy-1-naphthyl) and 1-(2-methylthio-1-naphthyl)isoquinoline: two new axially chiral NO and NS ligands for asymmetric catalysis

1999 ◽  
Vol 40 (3) ◽  
pp. 553-556 ◽  
Author(s):  
Giorgio Chelucci ◽  
Alessia Bacchi ◽  
Davide Fabbri ◽  
Antonio Saba ◽  
Fausta Ulgheri
Keyword(s):  
Asymmetric Catalysis ◽  
Enantiomerically Pure ◽  
Axially Chiral

Synthesis, characterization, and application in asymmetric catalysis of dendrimers containing chiral ferrocenyl diphosphines

2001 ◽  
Vol 79 (11) ◽  
pp. 1762-1774 ◽  
Author(s):  
Christoph Köllner ◽  
Antonio Togni
Keyword(s):  
Asymmetric Catalysis ◽  
Isophthalic Acid ◽  
Tricarboxylic Acid ◽  
Catalytic Reactions ◽  
Allylic Substitution ◽  
Asymmetric Catalytic ◽  
Ferrocenyl Ligands ◽  
The One ◽  
Parent Ligand ◽  
Dimethyl Itaconate

Starting from the functionalized Josiphos derivatives (R)-1-[(S)-2-(diphenylphosphino)-1'-(dimethyl-3''-aminopropylsilyl)-ferrocenyl]ethyldicyclohexylphosphine ((R)-(S)-3), (R)-1-[(S)-2-(diphenylphosphino)-1'-(hydroxy methyl) ferrocenyl]ethyldicyclohexylphosphine ((R)-(S)-4), and (R)-1-[(S)-2-(diphenylphosphino)-1'-(3''-hydroxy propyl)ferrocenyl]ethyldicyclohexylphosphine ((R)-(S)-5), a series of dendrimers containing up to sixteen ferrocenyl diphosphine units were prepared. Dendrimer cores are based on benzene 1,3,5-tricarboxylic acid and 1,3,5,7-adaman tanetetracarboxylic acid, with 5-substituted isophthalic acid derivatives constituting the branching units. The dendrimers have been used in three different asymmetric catalytic reactions: Rh-catalyzed hydrogenation of dimethyl itaconate, Pd-catalyzed allylic substitution, and Rh-catalyzed hydroboration of styrene with catecholborane. In all three reactions the selectivity obtained with the dendrimers was very similar to the one obtained with the parent ligand Josiphos.Key words: dendrimer, asymmetric catalysis, ferrocenyl ligands, hydrogenation.

Catalytic Atroposelective Dynamic Kinetic Resolution of Substituted Indoles

Synlett ◽  
2021 ◽  
Author(s):  
Ahreum Kim ◽  
Yongseok Kwon
Keyword(s):  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Ortho Position ◽  
Dynamic Kinetic Resolution ◽  
Research Attention ◽  
Considerable Research ◽  
Chiral Phosphoric Acid ◽  
Axially Chiral ◽  
High Yields ◽  
Enantioselective Syntheses

Advances in asymmetric catalysis have led to enormous progress in the atroposelective synthesis of axially chiral biaryls. Because of the biological importance of indoles, stereogenic axes in aryl-substituted indoles have attracted considerable research attention in recent years. Here we present a summary of recent advances in the atroposelective synthesis of aryl-substituted indoles by dynamic kinetic resolution. While several researchers have developed enantioselective syntheses of 3-arylindoles, N-arylindoles have been much less studied. Accordingly, we have reported a Pictet–Spengler reaction with catalytic and enantioselective control of the axial chirality around the C−N bond of the product. A chiral phosphoric acid induces the cyclization smoothly and with high yields and excellent enantioselectivities. To achieve this high selectivity, an NH group at the ortho position of the N-substituted aromatic ring that interacts favorably with the catalyst is required. Furthermore, when substituted aldehydes are used instead of paraformaldehyde, both the point and axial chiralities can be controlled during the cyclization.

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