A MESO SPECIFIC REACTION

Article abstract of DOI:10.1016/S0040-4039(00)84305-1

Acid-catalyzed condensation of optically pure 5-(hydroxymethyl)-2-pyrrolidinone, 2, with benzaldehyde gives only a monomeric optically active oxazolidine, 3, while under the same conditions, racemic 2 gives only a meso centrosymmetric compound 4 - a dimer of racemic 3.This meso specific reaction serves as a highly efficient method for increasing the optical purity of the generally useful chiral building blocks 2 and 3.