Pd-Catalyzed Asymmetric Allylic Alkylation of Pyrazol-5-ones with Allylic Alcohols: The Role of the Chiral Phosphoric Acid in C–O Bond Cleavage and Stereocontrol

2013 ◽  
Vol 135 (25) ◽  
pp. 9255-9258 ◽  
Author(s):  
Zhong-Lin Tao ◽  
Wen-Quan Zhang ◽  
Dian-Feng Chen ◽  
Arafate Adele ◽  
Liu-Zhu Gong
Keyword(s):  
Phosphoric Acid ◽  
Bond Cleavage ◽  
Allylic Alcohols ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Chiral Phosphoric Acid

scholarly journals Asymmetric Allylic Alkylation of β-Ketoesters via C–N Bond Cleavage of N-Allyl-N-methylaniline Derivatives Catalyzed by a Nickel–Diphosphine System

ACS Catalysis ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 5828-5839
Author(s):  
Haruki Nagae ◽  
Jingzhao Xia ◽  
Evgueni Kirillov ◽  
Kosuke Higashida ◽  
Koya Shoji ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation

Role of keto–enol tautomerization in a chiral phosphoric acid catalyzed asymmetric thiocarboxylysis of meso-epoxide: a DFT study

2015 ◽  
Vol 13 (45) ◽  
pp. 10981-10985 ◽  
Author(s):  
Manjaly J. Ajitha ◽  
Kuo-Wei Huang
Keyword(s):  
Density Functional Theory ◽  
Phosphoric Acid ◽  
Dft Calculations ◽  
Density Functional ◽  
Dft Study ◽  
Functional Theory ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

The mechanism of a chiral phosphoric acid catalyzed thiocarboxylysis of meso-epoxide was investigated by density functional theory (DFT) calculations (M06-2X).

scholarly journals Iridium-Catalyzed Asymmetric α-Allylic Alkylation of Amides using Vinyl Azide as Amide Enolate Surrogate

2020 ◽  
Author(s):  
Aditya Chakrabarty ◽  
Santanu Mukherjee
Keyword(s):  
Electronic Properties ◽  
Reaction Pathways ◽  
Allylic Alcohols ◽  
Allylic Alkylation ◽  
Atom Economy ◽  
Asymmetric Allylic Alkylation ◽  
Vinyl Azides ◽  
Alkylation Reactions ◽  
First Time

Among the unstabilized enolates used as nucleophile in iridium-catalyzed asymmetric allylic alkylation reactions, amide enolates are least explored. Vinyl azides are now employed as amide enolate surrogate for the first time in Ir-catalyzed asymmetric allylic alkylation with branched allylic alcohols as the allylic electrophile. Competing reaction pathways are suppressed through systematic tuning of steric and electronic properties of vinyl azide to effect α-allylic alkylation of secondary acetamides with high atom-economy, exclusive branched selectivity and moderate to excellent enantioselectivity.<br>

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