ChemInform Abstract: Organocatalytic Conversion of Arylglyoxals into Optically Active Mandelic Acid Derivatives.

ChemInform ◽  
2009 ◽  
Vol 40 (41) ◽  
Author(s):  
Ellen Schmitt ◽  
Ingo Schiffers ◽  
Carsten Bolm
Keyword(s):  
Mandelic Acid ◽  
Optically Active ◽  
Mandelic Acid Derivatives

Organocatalytic conversion of arylglyoxals into optically active mandelic acid derivatives

2009 ◽  
Vol 50 (26) ◽  
pp. 3185-3188 ◽  
Author(s):  
Ellen Schmitt ◽  
Ingo Schiffers ◽  
Carsten Bolm
Keyword(s):  
Mandelic Acid ◽  
Optically Active ◽  
Mandelic Acid Derivatives

Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Glyoxylates: Access to Optically Active Substituted Mandelic Acid Esters

Synlett ◽  
2019 ◽  
Vol 30 (14) ◽  
pp. 1693-1697
Author(s):  
Diao Chen ◽  
Jian-Guo Liu ◽  
Xu Zhang ◽  
Ming-Hua Xu
Keyword(s):  
Catalytic System ◽  
Mandelic Acid ◽  
Optically Active ◽  
Antiplatelet Drug ◽  
Reaction Conditions ◽  
Formal Synthesis ◽  
Arylboronic Acids ◽  
Synthetic Utility ◽  
Enantioselective Addition ◽  
Acid Esters

A rhodium-catalyzed enantioselective addition of glyoxylates to arylboronic acids promoted by a simple chiral sulfinamide-based olefin ligand under mild reaction conditions is described. The reaction provides access to a variety of optically active substituted mandelic acid esters in good yields with up to 83% ee. The catalytic system is also applicable to pyruvate addition. The synthetic utility of this method is highlighted by a formal synthesis of the antiplatelet drug clopidogrel.

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