N-Heterocyclic Carbene-Catalyzed [4 + 2] Cyclization of Saturated Carboxylic Acid with o-Quinone Methides through in Situ Activation: Enantioselective Synthesis of Dihydrocoumarins

2017 ◽  
Vol 82 (3) ◽  
pp. 1790-1795 ◽  
Author(s):  
Yuanfeng Wang ◽  
Jian Pan ◽  
Jingjiao Dong ◽  
Chenxia Yu ◽  
Tuanjie Li ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Enantioselective Synthesis ◽  
Quinone Methides ◽  
In Situ Activation

Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes

2020 ◽  
Vol 56 (3) ◽  
pp. 439-442 ◽  
Author(s):  
Yong You ◽  
Ting-Ting Li ◽  
Shu-Pei Yuan ◽  
Ke-Xin Xie ◽  
Zhen-Hua Wang ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Quinone Methides ◽  
Catalytic Asymmetric

An asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides enables the highly enantioselective synthesis of polysubstituted chromanes.

scholarly journals Chiral Brønsted acid-catalyzed Friedel–Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes

2015 ◽  
Vol 51 (8) ◽  
pp. 1461-1464 ◽  
Author(s):  
Satyajit Saha ◽  
Santosh Kumar Alamsetti ◽  
Christoph Schneider
Keyword(s):  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Reaction Conditions ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid ◽  
Hydrogen Bonded

Hydrogen-bonded, in situ-generated ortho-quinone methides undergo highly enantioselective Friedel–Crafts reactions with indoles and naphthols under mild reaction conditions.

scholarly journals Cu-catalyzed enantioselective synthesis of tertiary benzylic copper complexes and their in situ addition to carbonyl compounds

2018 ◽  
Vol 9 (22) ◽  
pp. 4992-4998 ◽  
Author(s):  
Fengchang Cheng ◽  
Wenxin Lu ◽  
Wei Huang ◽  
Lu Wen ◽  
Mingfeng Li ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Copper Complexes ◽  
Enantioselective Synthesis ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

Catalytic chemo- and enantioselective generation of tertiary benzylic copper complexes from Cu–B(pin) (pin = pinacolato) additions to 1,1-disubstituted alkenes followed by in situ reactions with ketones and carboxylic acid phenol esters to construct multifunctional alkylboron compounds that contain quaternary stereogenic centers is presented.

A Photoactivatable α5β1-Specific Integrin Ligand

2018 ◽  
Author(s):  
Roshna Vakkeel ◽  
Aleeza Farrukh ◽  
Aranzazu del Campo
Keyword(s):  
Cellular Response ◽  
Light Exposure ◽  
Matrix Composition ◽  
Cellular Behavior ◽  
Dynamic Variations ◽  
In Situ Activation ◽  
Controlled Exposure ◽  
Cellular Behaviour ◽  
Integrin Ligand

In order to study how dynamic changes of α5β1 integrin engagement affect cellular behaviour, photoactivatable derivatives of α5β1 specific ligands are presented in this article. The presence of the photoremovable protecting group (PRPG) introduced at a relevant position for integrin recognition, temporally inhibits ligand bioactivity. Light exposure at cell-compatible dose efficiently cleaves the PRPG and restores functionality. Selective cell response (attachment, spreading, migration) to the activated ligand on the surface is achieved upon controlled exposure. Spatial and temporal control of the cellular response is demonstrated, including the possibility to in situ activation. Photoactivatable integrin-selective ligands in model microenvironments will allow the study of cellular behavior in response to changes in the activation of individual integrins as consequence of dynamic variations of matrix composition.

Modular, Stereocontrolled Cβ–H/Cα–C Activation of Alkyl Carboxylic Acids

2019 ◽  
Author(s):  
Ming Shang ◽  
Karla S. Feu ◽  
Julien C. Vantourout ◽  
Lisa M. Barton ◽  
Heather L. Osswald ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Carbon Centers ◽  
Drug Candidates ◽  
Rapid Diversification ◽  
Directing Group ◽  
Compound Series

<div> <div> <div> <p>The union of two powerful transformations, directed C–H activation and decarboxylative cross-coupling, for the enantioselective synthesis of vicinally functionalized alkyl, carbocyclic, and heterocyclic compounds is described. Starting from simple carboxylic acid building blocks, this modular sequence exploits the residual directing group to access more than 50 scaffolds that would be otherwise extremely difficult to prepare. The tactical use of these two transformations accomplishes a formal vicinal difunctionalization of carbon centers in a way that is modular and thus amenable to rapid diversity incorporation. A simplification of routes to known preclinical drug candidates is presented along with the rapid diversification of an antimalarial compound series. </p> </div> </div> </div>

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