ChemInform Abstract: Chiral Integrated Catalysts Composed of Bifunctional Thiourea and Arylboronic Acid: Asymmetric Aza-Michael Addition of α,β-Unsaturated Carboxylic Acids.

ChemInform ◽  
2016 ◽  
Vol 47 (45) ◽  
Author(s):  
Noboru Hayama ◽  
Takumi Azuma ◽  
Yusuke Kobayashi ◽  
Yoshiji Takemoto
Keyword(s):  
Carboxylic Acids ◽  
Michael Addition ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

scholarly journals A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

2020 ◽  
Vol 11 (21) ◽  
pp. 5572-5576 ◽  
Author(s):  
Noboru Hayama ◽  
Yusuke Kobayashi ◽  
Eriko Sekimoto ◽  
Anna Miyazaki ◽  
Kiyofumi Inamoto ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Michael Addition ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

scholarly journals Mechanistic Insight into Asymmetric Hetero-Michael Addition of α,β-Unsaturated Carboxylic Acids Catalyzed by Multifunctional Thioureas

2018 ◽  
Vol 140 (38) ◽  
pp. 12216-12225 ◽  
Author(s):  
Noboru Hayama ◽  
Ryuta Kuramoto ◽  
Tamás Földes ◽  
Kazuya Nishibayashi ◽  
Yusuke Kobayashi ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Michael Addition ◽  
Mechanistic Insight ◽  
Unsaturated Carboxylic Acids ◽  
Insight Into

A Dual Arylboronic Acid–Aminothiourea Catalytic System for the Asymmetric Intramolecular Hetero-Michael Reaction of α,β-Unsaturated Carboxylic Acids

2014 ◽  
Vol 16 (16) ◽  
pp. 4256-4259 ◽  
Author(s):  
Takumi Azuma ◽  
Akihiro Murata ◽  
Yusuke Kobayashi ◽  
Tsubasa Inokuma ◽  
Yoshiji Takemoto
Keyword(s):  
Carboxylic Acids ◽  
Catalytic System ◽  
Michael Reaction ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

2020 ◽  
Author(s):  
Kiron Kumar Ghosh ◽  
Alexander Uttry ◽  
Francesca Ghiringhelli ◽  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Michael Addition ◽  
Kinetic Studies ◽  
Wide Range ◽  
Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

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