ChemInform Abstract: Boronic Acid-Catalyzed, Highly Enantioselective Aza-Michael Additions of Hydroxamic Acid to Quinone Imine Ketals.

ChemInform ◽  
2016 ◽  
Vol 47 (24) ◽  
Author(s):  
Takuya Hashimoto ◽  
Alberto Osuna Galvez ◽  
Keiji Maruoka
Keyword(s):  
Boronic Acid ◽  
Hydroxamic Acid ◽  
Quinone Imine ◽  
Michael Additions ◽  
Acid Catalyzed

Boronic-Acid-Catalyzed Regioselective and 1,2-cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via SNi-Type Mechanism

2018 ◽  
Vol 140 (10) ◽  
pp. 3644-3651 ◽  
Author(s):  
Masamichi Tanaka ◽  
Akira Nakagawa ◽  
Nobuya Nishi ◽  
Kiyoko Iijima ◽  
Ryuichi Sawa ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Stereoselective Glycosylation ◽  
Acid Catalyzed

A new and practical boronic acid catalyzed intramolecular cyclodehydration of ureas for the synthesis of LFA-1 antagonists

2011 ◽  
Vol 52 (19) ◽  
pp. 2465-2467 ◽  
Author(s):  
Rogelio P. Frutos ◽  
Thomas Tampone ◽  
Jason A. Mulder ◽  
Yibo Xu ◽  
Diana Reeves ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Acid Catalyzed

ChemInform Abstract: Boronic Acid Catalyzed Friedel-Crafts Reactions of Allylic Alcohols with Electron-Rich Arenes and Heteroarenes.

ChemInform ◽  
2010 ◽  
Vol 41 (22) ◽  
pp. no-no
Author(s):  
J. Adam McCubbin ◽  
Hamidreza Hosseini ◽  
Oleg V. Krokhin
Keyword(s):  
Boronic Acid ◽  
Allylic Alcohols ◽  
Acid Catalyzed

The ortho-substituent on 2,4-bis(trifluoromethyl)phenylboronic acid catalyzed dehydrative condensation between carboxylic acids and amines

2018 ◽  
Vol 54 (43) ◽  
pp. 5410-5413 ◽  
Author(s):  
Ke Wang ◽  
Yanhui Lu ◽  
Kazuaki Ishihara
Keyword(s):  
Carboxylic Acids ◽  
Boron Atom ◽  
Boronic Acid ◽  
Phenylboronic Acid ◽  
Acid Catalyzed ◽  
Ortho Substituent

The ortho-substituent of boronic acid plays a key role in preventing the coordination of amines to the boron atom.

scholarly journals Origin of Enantioselectivity Reversal in Lewis Acid-Catalyzed Michael Additions Relying on the Same Chiral Source

2020 ◽  
Author(s):  
Paul S. Riehl ◽  
Alistair D. Richardson ◽  
Tatsuhiro Sakamoto ◽  
Jolene P. Reid ◽  
Corinna Schindler
Keyword(s):  
Asymmetric Catalysis ◽  
Lewis Acid ◽  
Chiral Ligand ◽  
Potential Significance ◽  
Kinetics And Thermodynamics ◽  
Important Concept ◽  
Michael Additions ◽  
Acid Catalyzed ◽  
Mechanistic Understanding

Enantiodivergence is an important concept in asymmetric catalysis that enables access to both enantiomers of a product relying on the same chiral source. This strategy is particularly appealing as an alternate approach when only one enantiomer of the required chiral ligand is readily accessible but both enantiomers of the product are desired. Despite their potential significance, general catalytic methods to induce reversal in enantioselectivity remain underdeveloped. Herein we report our studies focused on elucidating the origin of enantioselectivity reversal in Lewis acid-catalyzed Michael additions relying on the same enantiomer of ligand as the chiral source. Our results provide a detailed mechanistic understanding of this transformation based on experimental and computational investigations which reveal the important interplay between kinetics and thermodynamics responsible for the observed enantiodivergence.

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