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

Synthesis of Axially Chiral 2,2’-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution

2020 ◽  
Author(s):  
Ziqing Zuo ◽  
Raphael Kim ◽  
Donald Watson
Keyword(s):  
Optical Resolution ◽  
Chiral Ligands ◽  
Chiral Auxiliaries ◽  
Axially Chiral ◽  
Ullmann Coupling

<div><p>We report an asymmetric Ullmann-type homocoupling of <i>ortho-</i>(iodo)arylphosphine oxides and <i>ortho</i>-(iodo)arylphosphonates that results in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates in good yields and excellent enantioselectivities. These products are readily converted to enantioenriched biaryl bisphosphines without need for chiral auxiliaries or optical resolution. This process provides a straightforward and practical route for the development of previously uninvestigated atroposelective biaryl bisphosphine ligands.</p></div>

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.

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

scholarly journals Convenient Optical Resolution of Axially Chiral 1,1′-Binaphthyl-2,2′-dicarboxylic Acid

1988 ◽  
Vol 61 (3) ◽  
pp. 1032-1034 ◽  
Author(s):  
Shigeyoshi Kanoh ◽  
Yukihiko Hongoh ◽  
Masatoshi Motoi ◽  
Hiroshi Suda
Keyword(s):  
Dicarboxylic Acid ◽  
Optical Resolution ◽  
Axially Chiral

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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