Lewis Acid Catalyzed Intramolecular Allylic Substitution of Bis(trichloroacetimidates): A Versatile Approach to Racemic Unsaturated Amino Acids

2011 ◽  
Vol 2011 (13) ◽  
pp. 2421-2425 ◽  
Author(s):  
Liene Grigorjeva ◽  
Aigars Jirgensons
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Allylic Substitution ◽  
Acid Catalyzed ◽  
Unsaturated Amino Acids

Critical role of Bronsted acid in Lewis-acid-catalyzed synthesis of Amadori and Heyns compounds of β-amino acids

2021 ◽  
pp. 1-11
Author(s):  
Debasree Chanda ◽  
Gangothri M. Venkataswamy ◽  
Lagamawwa V. Hipparagi ◽  
Nanishankar V. Harohally
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Critical Role ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

Syntheses of protected vinylic amino acids by intermolecular Lewis acid catalyzed ene reactions

1985 ◽  
Vol 26 (26) ◽  
pp. 3115-3118 ◽  
Author(s):  
K. Agouridas ◽  
J.M. Girodeau ◽  
R. Pineau
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Ene Reactions ◽  
Acid Catalyzed

Synthesis of dipeptides containing α-substituted amino acids; their use as chiral ligands in Lewis-acid-catalyzed reactions

2010 ◽  
Vol 114 (4-5) ◽  
pp. 231-238 ◽  
Author(s):  
Bernard Kaptein ◽  
Vania Monaco ◽  
Quirinus B. Broxterman ◽  
Hans E. Schoemaker ◽  
Johan Kamphuis
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Chiral Ligands ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

scholarly journals Chiral Tetrahydropyridines via FeCl3-Catalyzed Carbonyl-Olefin Metathesis

2019 ◽  
Author(s):  
Katie Rykaczewski ◽  
Emilia J. Groso ◽  
Hannah L. Vonesh ◽  
Mario Gaviria ◽  
Alistair D. Richardson ◽  
...  
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Olefin Metathesis ◽  
Unnatural Amino Acids ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Reaction Proceeds ◽  
Acid Catalyzed

<div> <div> <p>Herein, we describe the application of Lewis acid-catalyzed carbonyl-olefin metathesis towards the synthesis of chiral, substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl<sub>3</sub> as an inexpensive and environmentally benign catalyst and enables access to a variety of substituted tetrahydropyridines under mild reaction conditions. The reaction proceeds with complete stereoretention and is viable for a variety of natural and unnatural amino acids to provide the corresponding tetrahydropyridines in up to 99% yield.</p> </div> </div> <br>

Synthesis of α-Hydroxy Amides

2015 ◽  
Vol 729 ◽  
pp. 83-86 ◽  
Author(s):  
Dong Ming Lu ◽  
Zhi Jie Li ◽  
Feng Jiao Li ◽  
Qing Le Zeng
Keyword(s):  
Amino Acids ◽  
Organic Synthesis ◽  
Lewis Acid ◽  
Hydroxy Acids ◽  
Preparation Methods ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

α-Hydroxy amides are a class of important intermediates in organic synthesis. It plays an important role in the field of science and medicine. However, the preparation methods of α-hydroxy amides are relatively few, and they are usually enzyme-or Lewis acid-catalyzed reactions. These types of methods are not ideal in operation, yield and/or stereoselectivity. We found a new way to synthesize α-hydroxy amides by transforming amino acids into α-hydroxyl acids, and then by amination of the α-hydroxy acids.

scholarly journals Chiral Tetrahydropyridines via FeCl3-Catalyzed Carbonyl-Olefin Metathesis

2019 ◽  
Author(s):  
Katie Rykaczewski ◽  
Emilia J. Groso ◽  
Hannah L. Vonesh ◽  
Mario Gaviria ◽  
Alistair D. Richardson ◽  
...  
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Olefin Metathesis ◽  
Unnatural Amino Acids ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Reaction Proceeds ◽  
Acid Catalyzed

<div> <div> <p>Herein, we describe the application of Lewis acid-catalyzed carbonyl-olefin metathesis towards the synthesis of chiral, substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl<sub>3</sub> as an inexpensive and environmentally benign catalyst and enables access to a variety of substituted tetrahydropyridines under mild reaction conditions. The reaction proceeds with complete stereoretention and is viable for a variety of natural and unnatural amino acids to provide the corresponding tetrahydropyridines in up to 99% yield.</p> </div> </div> <br>

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