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Organocatalytic conversion of arylglyoxals into optically active mandelic acid derivatives

✍ Scribed by Ellen Schmitt; Ingo Schiffers; Carsten Bolm

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
342 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

A novel protocol for the organocatalytic conversion of arylglyoxals into the corresponding a-hydroxy arylacetic acid methyl esters has been developed. The catalyst consists of a combination of a commercially available cinchona alkaloid derivative and an achiral thiol and leads to enantiomerically enriched products (ee max 83%) under mild reaction conditions. The alkaloid can be easily recovered and reused without loss in activity and selectivity.

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## Abstract The presence of the silyl group plays a crucial role as it increases the reactivity and completely controls the regioselectivity of the desired arylation.