ChemInform Abstract: Catalytic Asymmetric Synthesis of Polysubstituted Spirocyclopropyl Oxindoles: Organocatalysis versus Transition Metal Catalysis

ChemInform ◽  
2015 ◽  
Vol 46 (34) ◽  
pp. no-no
Author(s):  
Zhong-Yan Cao ◽  
Jian Zhou
Keyword(s):  
Transition Metal ◽  
Asymmetric Synthesis ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Catalytic Asymmetric Synthesis ◽  
Versus Transition ◽  
Catalytic Asymmetric

Catalytic asymmetric synthesis of polysubstituted spirocyclopropyl oxindoles: organocatalysis versus transition metal catalysis

2015 ◽  
Vol 2 (7) ◽  
pp. 849-858 ◽  
Author(s):  
Zhong-Yan Cao ◽  
Jian Zhou
Keyword(s):  
Transition Metal ◽  
Asymmetric Synthesis ◽  
Recent Progress ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Catalytic Asymmetric Synthesis ◽  
Versus Transition ◽  
Catalytic Asymmetric

Recent progress in catalytic asymmetric synthesis of spirocyclopropyl oxindoles via organocatalysis and transition metal catalysis are summarized and discussed.

scholarly journals Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

2016 ◽  
Vol 12 ◽  
pp. 1000-1039 ◽  
Author(s):  
Bin Yu ◽  
Hui Xing ◽  
De-Quan Yu ◽  
Hong-Min Liu
Keyword(s):  
Clinical Trials ◽  
Natural Products ◽  
Drug Discovery ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Biological Activities ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric

Oxindole scaffolds are prevalent in natural products and have been recognized as privileged substructures in new drug discovery. Several oxindole-containing compounds have advanced into clinical trials for the treatment of different diseases. Among these compounds, enantioenriched 3-hydroxyoxindole scaffolds also exist in natural products and have proven to possess promising biological activities. A large number of catalytic asymmetric strategies toward the construction of 3-hydroxyoxindoles based on transition metal catalysis and organocatalysis have been reported in the last decades. Additionally, 3-hydroxyoxindoles as versatile precursors have also been used in the total synthesis of natural products and for constructing structurally novel scaffolds. In this review, we aim to provide an overview about the catalytic asymmetric synthesis of biologically important 3-substituted 3-hydroxyoxindoles and 3-hydroxyoxindole-based further transformations.

Asymmetric desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones using transition metal catalysis

2021 ◽  
Author(s):  
Tao Shu ◽  
Janine Cossy
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Transition Metal Catalysis ◽  
Chiral Ligands ◽  
Domino Reactions ◽  
Metal Catalysis ◽  
Catalytic Asymmetric

This review is covering the recent development of catalytic asymmetric domino reactions for the desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones using transition metals and chiral ligands.

scholarly journals Asymmetric Synthesis of Stereogenic Phosphorus P(V) Centers Using Chiral Nucleophilic Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3661
Author(s):  
Ahmed Numan ◽  
Matthew Brichacek
Keyword(s):  
Transition Metal ◽  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Chemical Biology ◽  
Transition Metal Catalysis ◽  
Nucleophilic Catalysis ◽  
Metal Catalysis ◽  
Chiral Catalyst ◽  
Stereocontrolled Synthesis ◽  
Stereogenic Centers

Organophosphates have been widely used in agrochemistry, as reagents for organic synthesis, and in biochemistry. Phosphate mimics possessing four unique substituents, and thereby a chirality center, are useful in transition metal catalysis and as nucleotide therapeutics. The catalytic, stereocontrolled synthesis of phosphorus-stereogenic centers is challenging and traditionally depends on a resolution or use of stochiometric auxiliaries. Herein, enantioenriched phosphorus centers have been synthesized using chiral nucleophilic catalysis. Racemic H-phosphinate species were coupled with nucleophilic alcohols under halogenating conditions. Chiral phosphonate products were synthesized in acceptable yields (33–95%) and modest enantioselectivity (up to 62% ee) was observed after identification of an appropriate chiral catalyst and optimization of the solvent, base, and temperature. Nucleophilic catalysis has a tremendous potential to produce enantioenriched phosphate mimics that could be used as prodrugs or chemical biology probes.

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