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

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.

2019 ◽  
Vol 17 (25) ◽  
pp. 6069-6098 ◽  
Author(s):  
Jin-Kui Liu ◽  
Jun-Fang Gong ◽  
Mao-Ping Song

This review covers the methods for the preparation of chiral palladium(ii) pincer complexes and their applications in asymmetric catalysis.


2017 ◽  
Vol 4 (3) ◽  
pp. 326-358 ◽  
Author(s):  
Yuanyuan Liu ◽  
Wenbo Li ◽  
Junliang Zhang

Abstract Asymmetric catalysis has become an indispensable and productive field within the Chinese organic chemistry society. The design of chiral ligands is one of the most prominent research areas in this field. Since the late 1990s, Chinese organic chemists have developed numerous chiral ligands possessing novel chiral skeletons and design concepts. Some of these ligands have been widely adopted and can be regarded as ‘privileged ligand’, which have shown excellent performance in many asymmetric catalytic reactions. In this review, we provide an overview of the chiral ligands designed by Chinese scientists with the aim of promoting the development of this area in China and with the hope of encouraging more scientists across the world to use these ligands when designing asymmetric reactions.


Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 869-874 ◽  
Author(s):  
Subramani Rajkumar ◽  
Jiawen Wang ◽  
Xiaoyu Yang

2-Aminoallyl cations are reactive intermediates that undergo diverse reactions, such as cycloadditions, direct nucleophilic additions, Nazarov electrocyclizations, and rearrangements. We review recent development in asymmetric catalytic reactions (nucleophilic additions and Nazarov electrocyclizations) based on chiral counteranion-paired 2-aminoallyl cation intermediates generated through activation of α-hydroxy enamides in the presence of chiral Brønsted acid catalysts. With an understanding of their asymmetric catalysis modes and mechanisms, we expect more asymmetric catalytic reactions will be developed on the basis of this strategy in the near future.


2020 ◽  
Vol 24 (20) ◽  
pp. 2341-2355
Author(s):  
Thaipparambil Aneeja ◽  
Sankaran Radhika ◽  
Mohan Neetha ◽  
Gopinathan Anilkumar

One-pot syntheses are a simple, efficient and easy methodology, which are widely used for the synthesis of organic compounds. Imidazoline is a valuable heterocyclic moiety used as a synthetic intermediate, chiral auxiliary, chiral catalyst and a ligand for asymmetric catalysis. Imidazole is a fundamental unit of biomolecules that can be easily prepared from imidazolines. The one-pot method is an impressive approach to synthesize organic compounds as it minimizes the reaction time, separation procedures, and ecological impact. Many significant one-pot methods such as N-bromosuccinimide mediated reaction, ring-opening of tetrahydrofuran, triflic anhydrate mediated reaction, etc. were reported for imidazoline synthesis. This review describes an overview of the one-pot synthesis of imidazolines and covers literature up to 2020.


ChemInform ◽  
2016 ◽  
Vol 47 (18) ◽  
Author(s):  
Pauline Loxq ◽  
Eric Manoury ◽  
Rinaldo Poli ◽  
Eric Deydier ◽  
Agnes Labande

2010 ◽  
Vol 352 (14-15) ◽  
pp. 2599-2610 ◽  
Author(s):  
Konstantin N. Gavrilov ◽  
Sergey V. Zheglov ◽  
Eugenie A. Rastorguev ◽  
Nikolay N. Groshkin ◽  
Marina G. Maksimova ◽  
...  

2014 ◽  
Vol 4 (7) ◽  
pp. 1997-2005 ◽  
Author(s):  
R. Oost ◽  
J. Rong ◽  
A. J. Minnaard ◽  
S. R. Harutyunyan

New derivatives of copper complexes of Josiphos family ligands have been prepared and studied in asymmetric catalytic addition of Grignard reagents to enones, enoates and aromatic ketones.


2021 ◽  
Vol 10 (1) ◽  
pp. 39
Author(s):  
Xinhua Qi ◽  
Wenlong Yan ◽  
Zhibei Cao ◽  
Mingzhu Ding ◽  
Yingjin Yuan

Polyethylene terephthalate (PET) is a widely used plastic that is polymerized by terephthalic acid (TPA) and ethylene glycol (EG). In recent years, PET biodegradation and bioconversion have become important in solving environmental plastic pollution. More and more PET hydrolases have been discovered and modified, which mainly act on and degrade the ester bond of PET. The monomers, TPA and EG, can be further utilized by microorganisms, entering the tricarboxylic acid cycle (TCA cycle) or being converted into high value chemicals, and finally realizing the biodegradation and bioconversion of PET. Based on synthetic biology and metabolic engineering strategies, this review summarizes the current advances in the modified PET hydrolases, engineered microbial chassis in degrading PET, bioconversion pathways of PET monomers, and artificial microbial consortia in PET biodegradation and bioconversion. Artificial microbial consortium provides novel ideas for the biodegradation and bioconversion of PET or other complex polymers. It is helpful to realize the one-step bioconversion of PET into high value chemicals.


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