Catalytic Enantioselective Arylation of Glyoxylate with Arylsilanes: Practical Synthesis of Optically Active Mandelic Acid Derivatives

2010 ◽  
Vol 5 (11) ◽  
pp. 2346-2350 ◽  
Author(s):  
Kohsuke Aikawa ◽  
Yūta Hioki ◽  
Koichi Mikami
Keyword(s):  
Mandelic Acid ◽  
Optically Active ◽  
Practical Synthesis ◽  
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.

Synthesis and Resolution of a Chiral Diamine: 2,2′-(Propane-2,2-diyl)dipyrrolidine

Synthesis ◽  
2017 ◽  
Vol 49 (14) ◽  
pp. 3107-3111 ◽  
Author(s):  
Stefan Kirsch ◽  
Andreas Kotthaus ◽  
Frederic Ballaschk ◽  
Vjoni Stakaj ◽  
Fabian Mohr
Keyword(s):  
Title Compound ◽  
Mandelic Acid ◽  
Chiral Diamine ◽  
Practical Synthesis

A short and practical synthesis of a new chiral dipyrrolidine is presented. The three-step route includes a hydrogenation and a resolution with mandelic acid, which easily affords large quantities of the title compound.

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