Asymmetric Allylation of α-Ketoester-Derived N -Benzoylhydrazones Promoted by Chiral Sulfoxides/N -Oxides Lewis Bases: Highly Enantioselective Synthesis of Quaternary α-Substituted α-Allyl-α-Amino Acids

Chirality ◽  
2013 ◽  
Vol 25 (9) ◽  
pp. 529-540 ◽  
Author(s):  
Gloria Reyes-Rangel ◽  
Yamir Bandala ◽  
Fred García-Flores ◽  
Eusebio Juaristi
Keyword(s):  
Amino Acids ◽  
Enantioselective Synthesis ◽  
Asymmetric Allylation ◽  
Lewis Bases ◽  
Chiral Sulfoxides

scholarly journals Rapid Organocatalytic Chirality Analysis of Amines, Amino Acids, Alcohols, Amino Alcohols and Diols with Achiral Iso(thio)cyanate Probes

2021 ◽  
Author(s):  
Eryn Nelson ◽  
Jeffrey S. S. K. Formen ◽  
Christian Wolf
Keyword(s):  
Amino Acids ◽  
Absolute Configuration ◽  
Rapid Determination ◽  
Amino Alcohols ◽  
Enantioselective Synthesis ◽  
Widespread Occurrence ◽  
Chiral Compounds ◽  
New Methods ◽  
The Absolute

The widespread occurrence and significance of chiral compounds does not only require new methods for their enantioselective synthesis but also efficient tools that allow rapid determination of the absolute configuration,...

scholarly journals Peculiarities of promiscuous l-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids

2021 ◽  
Author(s):  
Shan Wang ◽  
Hai Deng
Keyword(s):  
Amino Acids ◽  
Organic Molecules ◽  
Stereoselective Synthesis ◽  
Enantioselective Synthesis ◽  
General Mechanism ◽  
Future Developments ◽  
Key Points ◽  
Biomaterial Science ◽  
One Step ◽  
Harsh Conditions

Abstract The introduction of β-hydroxy-α-amino acids (βHAAs) into organic molecules has received considerable attention as these molecules have often found widespread applications in bioorganic chemistry, medicinal chemistry and biomaterial science. Despite innovation of asymmetric synthesis of βHAAs, stereoselective synthesis to control the two chiral centres at Cα and Cβ positions is still challenging, with poor atomic economy and multi protection and deprotection steps. These syntheses are often operated under harsh conditions. Therefore, a biotransformation approach using biocatalysts is needed to selectively introduce these two chiral centres into structurally diverse molecules. Yet, there are few ways that enable one-step synthesis of βHAAs. One is to extend the substrate scope of the existing enzyme inventory. Threonine aldolases have been explored to produce βHAAs. However, the enzymes have poor controlled installation at Cβ position, often resulting in a mixture of diastereoisomers which are difficult to be separated. In this respect, l-threonine transaldolases (LTTAs) offer an excellent potential as the enzymes often provide controlled stereochemistry at Cα and Cβ positions. Another is to mine LTTA homologues and engineer the enzymes using directed evolution with the aim of finding engineered biocatalysts to accept broad substrates with enhanced conversion and stereoselectivity. Here, we review the development of LTTAs that incorporate various aldehyde acceptors to generate structurally diverse βHAAs and highlight areas for future developments. Key points • The general mechanism of the transaldolation reaction catalysed by LTTAs • Recent advances in LTTAs from different biosynthetic pathways • Applications of LTTAs as biocatalysts for production of βHAAs

Enantioselective Synthesis of β-Trifluoromethyl α-Amino Acids

2010 ◽  
Vol 12 (9) ◽  
pp. 2008-2011 ◽  
Author(s):  
Cyril Benhaim ◽  
Luc Bouchard ◽  
Guillaume Pelletier ◽  
John Sellstedt ◽  
Livia Kristofova ◽  
...  
Keyword(s):  
Amino Acids ◽  
Enantioselective Synthesis
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