Enantioselective Michael Reaction of Cyclic β-Ketoesters with Morita–Baylis–Hillman Derivatives Using a Phase-Transfer Catalyst

2018 ◽  
Vol 83 (18) ◽  
pp. 11191-11203 ◽  
Author(s):  
Ryukichi Takagi ◽  
Emi Fujii ◽  
Hirotoshi Kondo
Keyword(s):  
Michael Reaction ◽  
Phase Transfer ◽  
Phase Transfer Catalyst

scholarly journals Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

2018 ◽  
Vol 14 ◽  
pp. 593-602 ◽  
Author(s):  
Romain Sallio ◽  
Stéphane Lebrun ◽  
Frédéric Capet ◽  
Francine Agbossou-Niedercorn ◽  
Christophe Michon ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Phase Transfer ◽  
Benzodiazepine Receptor ◽  
Optically Active ◽  
Chiral Auxiliary ◽  
Phase Transfer Catalyst ◽  
Receptor Agonists ◽  
Michael Acceptor

A new asymmetric organocatalyzed intramolecular aza-Michael reaction by means of both a chiral auxiliary and a catalyst for stereocontrol is reported for the synthesis of optically active isoindolinones. A selected cinchoninium salt was used as phase-transfer catalyst in combination with a chiral nucleophile, a Michael acceptor and a base to provide 3-substituted isoindolinones in good yields and diastereomeric excesses. This methodology was applied to the asymmetric synthesis of a new pazinaclone analogue which is of interest in the field of benzodiazepine-receptor agonists.

β-cyclodextrin grafted on lignin as inverse phase transfer catalyst for the oxidation of benzyl alcohol in H2O

Tetrahedron ◽  
2016 ◽  
Vol 72 (14) ◽  
pp. 1773-1781 ◽  
Author(s):  
Zujin Yang ◽  
Xia Zhang ◽  
Xingdong Yao ◽  
Yanxiong Fang ◽  
Hongyan Chen ◽  
...  
Keyword(s):  
Benzyl Alcohol ◽  
Phase Transfer ◽  
Phase Transfer Catalyst ◽  
Oxidation Of Benzyl Alcohol ◽  
Inverse Phase Transfer Catalyst

Microwave Energy Pretreated In Situ Transesterification of Jatropha Curcas L in the Presence of Phase Transfer Catalyst

2014 ◽  
Vol 625 ◽  
pp. 267-270 ◽  
Author(s):  
Sintayehu Mekuria Hailegiorgis ◽  
Mahadzir Shuhaimi ◽  
Duvvuri Subbarao
Keyword(s):  
Statistical Model ◽  
Jatropha Curcas ◽  
Phase Transfer ◽  
Phase Transfer Catalyst ◽  
In Situ Transesterification ◽  
Heat Pretreatment ◽  
Seed Particles ◽  
Optimum Reaction ◽  
Microwave Heat

In the present work, microwave heat pretreatment of jatropha curcas seed particles and use of phase transfer catalyst (PTC) to enhance in-situ transesterification were utilized together. It was observed that use of alkaline BTMAOH as a PTC and microwave heat pretreatment of jatropha curcas seed particles had substantially increased the reaction rate of in-situ transesterification as compared to the reaction conducted with microwave untreated seeds in the absence of BTMAOH as a PTC. Statistical model equation was developed to investigate the interaction effect of reaction variables and establish optimum reaction condition. At optimum condition, experimentally obtained FAME yield (93.7±1.53% w/w) was in close agreement with statistical model predicted FAME yield (96.75%) at 38°C and 37 minutes of reaction time.

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