DBU-Promoted Cascade Selective Nucleophilic Addition/C–C Bond Cleavage/Hetero-Diels–Alder Reactions of 2-Amino-4H-chromen-4-ones with β-Nitrostyrenes and/or Aryl Aldehydes: Access to 5H-Chromeno[2,3-b]pyridin-5-ones

2020 ◽  
Vol 85 (21) ◽  
pp. 14219-14228
Author(s):  
Naili Luo ◽  
Shan Wang ◽  
Yue Zhang ◽  
Junhu Xin ◽  
Cunde Wang
Keyword(s):  
Nucleophilic Addition ◽  
Bond Cleavage ◽  
Diels Alder ◽  
Aryl Aldehydes

Chelation-control in nucleophilic addition to Cr(CO)3-complexed aryl aldehydes

2003 ◽  
Vol 1 (10) ◽  
pp. 1720-1725 ◽  
Author(s):  
Suresh Kumar Tipparaju ◽  
Vedavati G. Puranik ◽  
Amitabha Sarkar
Keyword(s):  
Nucleophilic Addition ◽  
Aryl Aldehydes

Preparations of Tryptamine-4,5-dinones, and Their Diels-Alder and Nucleophilic Addition Reactions

Heterocycles ◽  
1995 ◽  
Vol 41 (10) ◽  
pp. 2157 ◽  
Author(s):  
Masanori Somei ◽  
Yoshikazu Fukui ◽  
Masakazu Hasegawa
Keyword(s):  
Nucleophilic Addition ◽  
Diels Alder ◽  
Addition Reactions

scholarly journals A Cu(II)–ATP complex efficiently catalyses enantioselective Diels–Alder reactions

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Changhao Wang ◽  
Qianqian Qi ◽  
Wenying Li ◽  
Jingshuang Dang ◽  
Min Hao ◽  
...  
Keyword(s):  
Metal Complexes ◽  
Density Functional ◽  
Bond Cleavage ◽  
High Reactivity ◽  
Diels Alder ◽  
Functional Theory ◽  
Catalytic Mechanisms ◽  
Key Residues ◽  
Chemical Selection ◽  
Selection Of

Abstract Natural biomolecules have been used extensively as chiral scaffolds that bind/surround metal complexes to achieve stereoselectivity in catalytic reactions. ATP is ubiquitously found in nature as an energy-storing molecule and can complex diverse metal cations. However, in biotic reactions ATP-metal complexes are thought to function mostly as co-substrates undergoing phosphoanhydride bond cleavage reactions rather than participating in catalytic mechanisms. Here, we report that a specific Cu(II)-ATP complex (Cu2+·ATP) efficiently catalyses Diels-Alder reactions with high reactivity and enantioselectivity. We investigate the substrates and stereoselectivity of the reaction, characterise the catalyst by a range of physicochemical experiments and propose the reaction mechanism based on density functional theory (DFT) calculations. It is found that three key residues (N7, β-phosphate and γ-phosphate) in ATP are important for the efficient catalytic activity and stereocontrol via complexation of the Cu(II) ion. In addition to the potential technological uses, these findings could have general implications for the chemical selection of complex mixtures in prebiotic scenarios.

Copper-catalyzed aerobic oxidative cleavage of C–C bonds in epoxides leading to aryl nitriles and aryl aldehydes

2015 ◽  
Vol 51 (30) ◽  
pp. 6572-6575 ◽  
Author(s):  
Lijun Gu ◽  
Cheng Jin
Keyword(s):  
Bond Cleavage ◽  
Oxidative Cleavage ◽  
Single Bond ◽  
Aryl Aldehydes ◽  
Aryl Nitriles

Novel copper-catalyzed aerobic synthesis of aryl nitriles and aldehydes from epoxides via C–C single bond cleavage has been discovered.

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