Molecular Diversity of Tonghaosu Analogues, Selective Oxidation of the exo-Cyclic Double Bond of Spiroacetal Enol Ethers and Diasteroselective Synthesis of Spiro-Pyranone

2010 ◽  
Vol 28 (12) ◽  
pp. 2335-2338 ◽  
Author(s):  
Biaolin Yin ◽  
Jinqiang Lai ◽  
Zeren Zhang ◽  
Yulin Wu
Keyword(s):  
Double Bond ◽  
Selective Oxidation ◽  
Molecular Diversity ◽  
Enol Ethers

Double bond isomerizations in unsaturated esters and enol ethers. I. Equilibrium studies in cyclic and acyclic systems

1970 ◽  
Vol 35 (10) ◽  
pp. 3352-3358 ◽  
Author(s):  
Sara J. Rhoads ◽  
Jitendra K. Chattopadhyay ◽  
Edward E. Waali
Keyword(s):  
Double Bond ◽  
Equilibrium Studies ◽  
Enol Ethers ◽  
Unsaturated Esters

Selective Oxidation of Vinyl Ethers and Silyl Enol Ethers with Hydrogen Peroxide Catalyzed by Peroxotungstophosphate

1997 ◽  
Vol 62 (21) ◽  
pp. 7174-7177 ◽  
Author(s):  
Hiroyo Yamamoto ◽  
Masaya Tsuda ◽  
Satoshi Sakaguchi ◽  
Yasutaka Ishii
Keyword(s):  
Hydrogen Peroxide ◽  
Selective Oxidation ◽  
Vinyl Ethers ◽  
Enol Ethers ◽  
Silyl Enol Ethers

scholarly journals Design of Boradecarboxylation Reaction

2020 ◽  
Author(s):  
Yuji Naruse ◽  
Atsushi Takamori ◽  
Kenji Oda
Keyword(s):  
Double Bond ◽  
Theoretical Calculation ◽  
Polar Solvent ◽  
Theoretical Calculations ◽  
Lone Pair ◽  
Carbonyl Groups ◽  
Orbital Theory ◽  
Enol Ethers ◽  
Decarboxylation Reaction ◽  
Boat Form

For mechanism of decarboxylation reaction, all textbooks show that the electron moves from the pi<sub>C=O</sub> bond. However, the most donating bond orbital in the carbonyl group should be the lone pair(s) on the oxygen. Thus, a picture of orbital theory with delocalization from a lone pair should be more appropriate than that from the pi<sub>C=O</sub> orbital. We confirmed our idea by theoretical calculation. In the TS, if we use 2-substituted b-ketoacids, the boat-form conformation should result in exclusively preferred generation of <i>E</i>-enolates. Normally, decarboxylation reaction performs in polar solvent, so that the resulting enols should be transformed to the corresponding ketones by tautomerization. Suppose we use the heteroatoms to obtain the enolate or enol ethers without tautomerization, it would offer a diastereoselective enol(ate) synthesis with regioselectivity, since the C=C double bond should always be introduced between two carbonyl groups. After screening the heteroatoms by the theoretical calculations, we found that boron is suitable for this purpose. We confirmed our idea by theoretical calculations, offering a new boradecarboxylation reaction to produce enolates diastereoselecitively and regioselectively.

Accessing 1,2-Amino Alcohols and Diols through Photocatalytic Anti-Markovnikov Difunctionalisation of Ene-Carbamates and Enol Ethers

2020 ◽  
Author(s):  
Jerome Waser ◽  
Stefano Nicolai ◽  
Stephanie G. E. Amos
Keyword(s):  
Double Bond ◽  
Radical Cation ◽  
Amino Alcohol ◽  
Oxygen Transfer ◽  
Room Temperature ◽  
Organic Dye ◽  
Enol Ethers ◽  
Blue Led ◽  
Broad Variety ◽  
Led Irradiation

We report an atom-economical 1,2-oxyalkynylation of ene-carbamates and enol ethers based on the use of Ethynyl BenziodoXolone (EBX) as dual reagents for alkyne and oxygen transfer. The reaction occurs at room temperature under blue LED irradiation using an organic dye as a photocatalyst. A broad variety of 1-alkynyl-1,2-amino-alcohol and 1-alkynyl-1,2-diol scaffolds were obtained in up to 89% yield with anti-Markovnikov regioselectivity. The reaction is speculated to proceed via oxidation of the double bond to give a radical cation intermediate, enabling the selective difunctionalization of electron-rich alkenes.

scholarly journals Molecular Diversity of Alkenal Double Bond Reductases in the Liverwort Marchantia paleacea

Molecules ◽  
2018 ◽  
Vol 23 (7) ◽  
pp. 1630 ◽  
Author(s):  
Yi-Feng Wu ◽  
Hong-Bo Zheng ◽  
Xin-Yan Liu ◽  
Ai-Xia Cheng ◽  
Hong-Xiang Lou
Keyword(s):  
Double Bond ◽  
Molecular Diversity ◽  
Marchantia Paleacea
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