Resolution of a citric acid derivative: Synthesis of (R)-(-)-homocitric acid-γ-lactone

Article abstract of DOI:10.1016/S0957-4166(97)00435-7

Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in ≤90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-α-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)- homocitric acid utilising an Amdt-Eistert homologation followed by acid eatalysed deprotection.