Synthesis and application of P,olefin type axially chiral ligands with sec-alkyl groups

2019 ◽  
Vol 17 (6) ◽  
pp. 1455-1465 ◽  
Author(s):  
Takashi Mino ◽  
Daiki Yamaguchi ◽  
Chihiro Masuda ◽  
Junpei Youda ◽  
Toshibumi Ebisawa ◽  
...  
Keyword(s):  
Chiral Ligands ◽  
Chiral Ligand ◽  
Allylic Substitution ◽  
Alkyl Groups ◽  
Axially Chiral ◽  
Palladium Catalyzed

Palladium-catalyzed asymmetric allylic substitution with indoles using a chiral ligand 3b, which have fewer hindered substituents such as secondary alkyl groups than 1-adamantyl group, gave desired products (R)-9 with high enantioselectivities (up to 96% ee).

Design of bifunctional chiral phenanthroline ligand with Lewis basic site for palladium-catalyzed asymmetric allylic substitution

2018 ◽  
Vol 54 (21) ◽  
pp. 2674-2677 ◽  
Author(s):  
Yuki Naganawa ◽  
Hiroki Abe ◽  
Hisao Nishiyama
Keyword(s):  
Chiral Ligands ◽  
Basic Site ◽  
Allylic Substitution ◽  
Palladium Catalyzed ◽  
Phenanthroline Ligand

Conceptually new bifunctional chiral ligands with Lewis basic site were developed for Pd-catalyzed asymmetric allylic substitution.

Chiral P,Olefin Ligands with Rotamers for Palladium-Catalyzed Asymmetric Allylic Substitution Reactions

Synlett ◽  
2020 ◽  
Author(s):  
Takashi Mino ◽  
Daiki Yamaguchi ◽  
Manami Kumada ◽  
Junpei Youda ◽  
Hironori Saito ◽  
...  
Keyword(s):  
Chiral Ligands ◽  
Allylic Substitution ◽  
Substitution Reactions ◽  
Palladium Catalyzed

We synthesized a series of phosphine–olefin-type chiral aminophosphines, and we confirmed that these each exists as two rotamers at the C(aryl)–N(amine) bond. We also investigated the ability of these aminophosphines to act as chiral ligands for Pd-catalyzed asymmetric allylic substitution reactions, such as the alkylation of allylic acetates with malonates or indoles, and we found they gave high enantio­selectivities (up to 98% ee).

ChemInform Abstract: Novel Phosphinobioxazines as Chiral Ligands in Palladium-Catalyzed Enantioselective Allylic Substitution.

ChemInform ◽  
2010 ◽  
Vol 30 (42) ◽  
pp. no-no
Author(s):  
Sang-gi Lee ◽  
So Ha Lee ◽  
Choong Eui Song ◽  
Bong Young Chung
Keyword(s):  
Chiral Ligands ◽  
Allylic Substitution ◽  
Palladium Catalyzed

Novel phosphinobioxazines as chiral ligands in palladium-catalyzed enantioselective allylic substitution

1999 ◽  
Vol 10 (9) ◽  
pp. 1795-1802 ◽  
Author(s):  
Sang-gi Lee ◽  
So Ha Lee ◽  
Choong Eui Song ◽  
Bong Young Chung
Keyword(s):  
Chiral Ligands ◽  
Allylic Substitution ◽  
Palladium Catalyzed

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>

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