Enantioselective Equilibration−Access to Chiral Aldol Adducts of Mandelic 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.

Download Full-text

Simple and Efficient Synthesis of Racemic Substituted Mandelic Acid Esters from Nonactivated Arenes and Ethyl Glyoxylate

Synthesis ◽

10.1055/s-0028-1083154 ◽

2008 ◽

Vol 2008 (20) ◽

pp. 3237-3244

Author(s):

Janusz Jurczak ◽

Jacek Kwiatkowski ◽

Jakub Majer ◽

Piotr Kwiatkowski

Keyword(s):

Mandelic Acid ◽

Efficient Synthesis ◽

Acid Esters

Download Full-text

Catalytic Enantioselective Friedel−Crafts Reactions of Aromatic Compounds with Glyoxylate: A Simple Procedure for the Synthesis of Optically Active Aromatic Mandelic Acid Esters

Journal of the American Chemical Society ◽

10.1021/ja002593j ◽

2000 ◽

Vol 122 (50) ◽

pp. 12517-12522 ◽

Cited By ~ 130

Author(s):

Nicholas Gathergood ◽

Wei Zhuang ◽

Karl Anker Jørgensen

Keyword(s):

Aromatic Compounds ◽

Mandelic Acid ◽

Simple Procedure ◽

Optically Active ◽

Acid Esters

Download Full-text

Stereoselective Synthesis of 3-azabicyclo[3,3,1]Nonan-9α-yl α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate Hydrochloride

Journal of Chemical Research ◽

10.3184/0308234054323896 ◽

2005 ◽

Vol 2005 (5) ◽

pp. 322-323 ◽

Cited By ~ 5

Author(s):

He Liu ◽

Xiang-Yu Han ◽

Bo-Hua Zhong ◽

Ke-Liang Liu

Keyword(s):

Mandelic Acid ◽

Phenylacetic Acid ◽

Stereoselective Synthesis ◽

Enantiomeric Excess ◽

Starting Material ◽

Sterically Hindered ◽

Acid Esters

The isomers of α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetic acid esters derived from 3-azabicyclo[3,3,1]nonan-9α-ol ((R)-1 and (S)-1) were obtained in high enantiomeric excess by effective stereoselective synthesis from the chiral starting material, (S) or (R)-mandelic acid using pivaldehyde as a sterically hindered reagent

Download Full-text

ChemInform Abstract: Kinetic Resolution of Racemic Mandelic Acid Esters by N,N′-Dioxide-Scandium-Complex-Catalyzed Enantiomer-Selective Acylation.

ChemInform ◽

10.1002/chin.201517100 ◽

2015 ◽

Vol 46 (17) ◽

pp. no-no

Author(s):

Yuheng Zhang ◽

Xiaohua Liu ◽

Lin Zhou ◽

Wangbin Wu ◽

Tianyu Huang ◽

...

Keyword(s):

Mandelic Acid ◽

Kinetic Resolution ◽

Selective Acylation ◽

Acid Esters

Download Full-text

Plant-Mediated Stereoselective Biotransformation of Phenylglyoxylic Acid Esters

Zeitschrift für Naturforschung C ◽

10.5560/znc.2013-0192 ◽

2014 ◽

Vol 69 (7-8) ◽

pp. 309-316 ◽

Cited By ~ 2

Author(s):

Wanda Krystyna Mączka ◽

Małgorzata Grabarczyk ◽

Katarzyna Winśka ◽

Mirosław Anioł

Keyword(s):

Carbonyl Group ◽

Mandelic Acid ◽

High Yield ◽

Methyl Ethyl ◽

Phenylglyoxylic Acid ◽

Plant Materials ◽

Enantioselective Reduction ◽

Propyl Esters ◽

Acid Esters

Enantioselective reduction of the carbonyl group of three phenylglyoxylic acid esters (methyl, ethyl, and n-propyl esters, 2 - 4) was conducted using blended plant materials (roots of carrot, beetroot, celeriac and parsley; apple). All used biocatalysts transformed these esters to the corresponding mandelic acid esters with high yield, preferably into the respective R-enantiomer. Butanedione addition improved the enantioselectivity of the reaction.

Download Full-text