Lewis Acid-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions of Diazoalkane:  Chiral Ligand/Achiral Auxiliary Cooperative Chirality Control

2000 ◽  
Vol 122 (43) ◽  
pp. 10710-10711 ◽  
Author(s):  
Shuji Kanemasa ◽  
Toshio Kanai
Keyword(s):  
Lewis Acid ◽  
Chiral Ligand ◽  
Dipolar Cycloadditions ◽  
Acid Catalyzed ◽  
Chirality Control

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.

Ruthenium Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloadditions between N-Methylnitrones and Enals

Synthesis ◽  
2010 ◽  
Vol 2010 (13) ◽  
pp. 2207-2212 ◽  
Author(s):  
E. Kündig ◽  
Andrei Bãdoiu ◽  
Gérald Bernardinelli
Keyword(s):  
Lewis Acid ◽  
Dipolar Cycloadditions ◽  
Acid Catalyzed

Lewis Acid Catalyzed Dipolar Cycloadditions of an Activated Imidate

2004 ◽  
Vol 69 (24) ◽  
pp. 8537-8540 ◽  
Author(s):  
Roy K. Bowman ◽  
Jeffrey S. Johnson
Keyword(s):  
Lewis Acid ◽  
Dipolar Cycloadditions ◽  
Acid Catalyzed

scholarly journals Thermodynamic vs. Kinetic Control Enables Lewis Acid-Induced Enantioselectivity Reversal 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 ◽  
Kinetic Control ◽  
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.

ChemInform Abstract: Ruthenium Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloadditions Between N-Methylnitrones and Enals.

ChemInform ◽  
2010 ◽  
Vol 41 (44) ◽  
pp. no-no
Author(s):  
Andrei Badoiu ◽  
Gerald Bernardinelli ◽  
E. Peter Kuendig
Keyword(s):  
Lewis Acid ◽  
Dipolar Cycloadditions ◽  
Acid Catalyzed

scholarly journals Lewis Acid Catalyzed Dipolar Cycloadditions of an Activated Imidate.

ChemInform ◽  
2005 ◽  
Vol 36 (17) ◽  
Author(s):  
Roy K. Bowman ◽  
Jeffrey S. Johnson
Keyword(s):  
Lewis Acid ◽  
Dipolar Cycloadditions ◽  
Acid Catalyzed

scholarly journals Thermodynamic vs. Kinetic Control Enables Lewis Acid-Induced Enantioselectivity Reversal 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 ◽  
Kinetic Control ◽  
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.

scholarly journals Asymmetric Lewis acid-catalyzed 1,3-dipolar cycloadditions

2008 ◽  
Vol 80 (5) ◽  
pp. 1013-1018 ◽  
Author(s):  
Andrei Bădoiu ◽  
Yasmin Brinkmann ◽  
Florian Viton ◽  
E. Peter Kündig
Keyword(s):  
Transition Metal ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Asymmetric Catalytic ◽  
Aldehydes And Ketones ◽  
Acid Catalyzed

Highly tuned, one-point binding chiral iron and ruthenium complexes selectively coordinate and activate α,β-unsaturated aldehydes and ketones toward asymmetric catalytic Diels-Alder cycloaddition reactions. Here we focus on the application of these transition-metal Lewis acids to asymmetric catalytic 1,3-dipolar cycloaddition reaction between enals and cyclic and acyclic nitrones as well as aryl nitrile oxides to give isoxazolidines and isoxazolines, respectively.

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