Transition-Metal- and Light-Free Generation of an Iminyl Radical: Facile Approach to Oxindoles and Isoquinolinediones with a Quaternary Carbon Center via Cyanoalkylarylation

2021 ◽  
Author(s):  
Lanjun Su ◽  
Pan Xue ◽  
Xin Zhu ◽  
Huan Sun ◽  
Jikai Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Quaternary Carbon ◽  
Free Generation

scholarly journals Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis

2017 ◽  
Vol 117 (19) ◽  
pp. 12564-12580 ◽  
Author(s):  
Jiajie Feng ◽  
Michael Holmes ◽  
Michael J. Krische
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Quaternary Carbon ◽  
Metal Catalysis

DBU-promoted ring-opening reactions of multi-substituted donor–acceptor cyclopropanes: access to functionalized chalcones with a quaternary carbon group

2020 ◽  
Vol 18 (45) ◽  
pp. 9210-9215
Author(s):  
Naili Luo ◽  
Jiamin Liu ◽  
Shan Wang ◽  
Cunde Wang
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Metal Catalyst ◽  
Quaternary Carbon ◽  
Transition Metal Catalyst ◽  
Ring Opening Reactions ◽  
Donor Acceptor

A strategy to synthesize highly stereoselective chalcones with alkylcyanoacetate subunits via DBU-promoted ring-opening reactions of multi-substituted D–A cyclopropanes has been developed without the requirement of a transition metal catalyst and extra solvent.

Asymmetric Synthesis of a Bicyclo[4.3.0]nonene Derivative Bearing a Quaternary Carbon Stereocenter: Desymmetrization of σ-Symmetrical Diketones through Intramolecular Addition of an Alkenyl Anion

Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3667-3674
Author(s):  
Tomoyuki Yoshimura ◽  
Yuki Enami ◽  
Jun-ichi Matsuo
Keyword(s):  
Transition Metal ◽  
Asymmetric Synthesis ◽  
Transition Metal Complexes ◽  
Nucleophilic Addition ◽  
Enantioselective Synthesis ◽  
Chiral Ligand ◽  
Bicyclic Compound ◽  
Carbonyl Groups ◽  
Quaternary Carbon ◽  
Complementary Approach

The enantioselective synthesis of a bicyclo[4.3.0]nonene derivative bearing a quaternary carbon stereocenter is achieved by employing a desymmetrization strategy involving an intramolecular addition. The intramolecular nucleophilic addition of a highly reactive carbanion generated from an alkenyl iodide in the presence of a chiral ligand occurs with discrimination of two keto carbonyl groups to give the corresponding bicyclic compound in 81% yield and 39% ee. Asymmetric synthesis via an intramolecular desymmetrization strategy using a chiral ligand–carbanion complex represents a complementary approach to using chiral organocatalysts or chiral ligand–transition-metal complexes.

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