Enantioselective Synthesis of a Novel Chiral 2,9-Disubstituted 1,10-Phenanthroline and First Applications in Asymmetric Catalysis

2009 ◽  
Vol 2009 (36) ◽  
pp. 6393-6398 ◽  
Author(s):  
Mecheril Valsan Nandakumar ◽  
Subrata Ghosh ◽  
Christoph Schneider
Keyword(s):  
Asymmetric Catalysis ◽  
Enantioselective Synthesis

Novel Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation/ Asymmetric Tsuji-Trost Reaction: A Review

2019 ◽  
Vol 23 (11) ◽  
pp. 1168-1213 ◽  
Author(s):  
Samar Noreen ◽  
Ameer Fawad Zahoor ◽  
Sajjad Ahmad ◽  
Irum Shahzadi ◽  
Ali Irfan ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Enantioselective Synthesis ◽  
Chiral Ligands ◽  
Allylic Alkylation ◽  
Research Groups ◽  
Asymmetric Allylic Alkylation ◽  
Catalytic Potential ◽  
Long Time ◽  
Palladium Catalyzed ◽  
Alkylation Reactions

Background: Asymmetric catalysis holds a prestigious role in organic syntheses since a long time and chiral inductors such as ligands have been used to achieve the utmost desired results at this pitch. The asymmetric version of Tsuji-Trost allylation has played a crucial role in enantioselective synthesis. Various chiral ligands have been known for Pdcatalyzed Asymmetric Allylic Alkylation (AAA) reactions and exhibited excellent catalytic potential. The use of chiral ligands as asymmetric inductors has widened the scope of Tsuji-Trost allylic alkylation reactions. Conclusion: Therefore, in this review article, a variety of chiral inductors or ligands have been focused for palladium catalyzed asymmetric allylic alkylation (Tsuji-Trost allylation) and in this regard, recently reported literature (2013-2017) has been described. The use of ligands causes the induction of enantiodiscrimination to the allylated products, therefore, the syntheses of various kinds of ligands have been targeted by many research groups to employ in Pd-catalyzed AAA reactions.

scholarly journals Catalytic Enantioselective Synthesis of 4-Amino-1,2,3,4-tetrahydropyridine Derivatives from Intramolecular Nucleophilic Addition Reaction of Tertiary Enamides

Synlett ◽  
2018 ◽  
Vol 30 (04) ◽  
pp. 483-487 ◽  
Author(s):  
Shuo Tong ◽  
Mei-Xiang Wang
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Catalysis ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Substrate Engineering ◽  
Nucleophilic Addition Reaction ◽  
Engineering Strategy ◽  
Acid Catalyzed

A general and efficient method for the synthesis of highly enantiopure 4-amino-1,2,3,4-tetradydropyridine derivatives based on chiral phosphoric acid catalyzed intramolecular nucleophilic addition of tertiary enamides to imines has been developed. We have also demonstrated a substrate engineering strategy to significantly improve the enantioselectivity of asymmetric catalysis

Deconjugated butenolide: a versatile building block for asymmetric catalysis

2020 ◽  
Vol 49 (18) ◽  
pp. 6755-6788 ◽  
Author(s):  
Abhijnan Ray Choudhury ◽  
Santanu Mukherjee
Keyword(s):  
Asymmetric Catalysis ◽  
Building Block ◽  
Enantioselective Synthesis ◽  
Asymmetric Reactions ◽  
Comprehensive Overview ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Reactions

Deconjugated butenolides have emerged as a popular synthon for the enantioselective synthesis of γ-lactones. This review provides a comprehensive overview on the catalytic asymmetric reactions of deconjugated butenolides reported till date.

scholarly journals Organocatalytic Discrimination of Non-Directing Aryl and Heteroaryl Groups: Enantioselective Synthesis of Bioactive Indole-Containing Triarylmethanes

2021 ◽  
Author(s):  
Qiaolin Yan ◽  
Meng Duan ◽  
Cien Chen ◽  
Zhiqin Deng ◽  
Mandi Wu ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Spatial Interaction ◽  
Antiviral Drug ◽  
Kinetic Studies ◽  
Enantioselective Synthesis ◽  
Asymmetric Induction ◽  
Efficient Access ◽  
Chiral Phosphoric Acid ◽  
Biological Studies ◽  
Directing Group

Despite the enormous developments of asymmetric catalysis, the basis for asymmetric induction is largely limited to spatial interaction between substrate and catalyst. Consequently, asymmetric discrimination between two sterically similar groups remains a challenge. This is particularly formidable for enantiodifferentiation between aryl and heteroaryl groups without a directing group or electronic manipulation. Here we address this challenge by a robust organocatalytic system leading to excellent enantioselection between aryl and heteroaryl groups. With the versatile 2-indole imine methide as platform, an excellent combination of a superb chiral phosphoric acid and the optimal hydride source provided efficient access to a range of highly enantioenriched indole-containing triarylmethanes. Control experiments and kinetic studies provided important insights into the mechanism. DFT calculations also indicated that, while hydrogen bonding is important for activation, the key interaction for discrimination of the two aryl groups is mainly π-π stacking. Preliminary biological studies also demonstrated the great potential of these triarylmethanes for anticancer and antiviral drug development.

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