Article(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries for the asymmetric synthesis of α-hydroxy acids

Add time:09/24/2019    Source:sciencedirect.com

Rac-α-bromo acids, rac-4, have been converted into (R)- or (S)-α-hydroxy acid, (R)- or (S)-9, by DCC-induced esterification with the chiral auxiliaries (R)- or (S)-1, followed by reaction with sodium p-methoxyphenoxide in the presence of tetra-n-hexylammonium iodide, conditions of dynamic kinetic resolution, to give quite diastereoselectively the (αR,3S)- or (αS,3R)-α-(p-methoxyphenoxy) esters, 7, which were then oxidized with ceric ammonium nitrate and hydrolyzed under controlled acid conditions.

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