(2R,3R)-2-Amino-3-cyclohexyl-3-hydroxypropionic acid, a β-hydroxy-α-amino acid in a new CCR5 antagonist, was efficiently synthesized by the Noyori asymmetric hydrogenation of a-benzoylamino-β-keto ester (6) and intramolecular S N 2-type inversion as the key steps.

This study demonstrates a highly stereoselective synthesis of (2R,3R)-2-amino-3-cyclohexyl-3-hydroxypropionic acid using asymmetric hydrogenation and intramolecular S N 2-type inversion, providing a potential CCR5 antagonist.

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Highly stereoselective synthesis of (2R,3R)-2-amino-3-cyclohexyl-3-hydroxypropionic acid using asymmetric hydrogenation

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