EFFECT OF AGGREGATION ON STEREOCHEMISTRY AND MECHANISM OF ASYMMETRIC OXIDATION OF THE LITHIUM ENOLATE OF METHYL 3,3-DIMETHYLBUTANOATE IN THE SOLID STATE AND IN SOLUTION

Article abstract of DOI:10.1016/S0040-4039(00)79208-2

Oxidation of the title enolate by enantiopure (camphorylsulfonyl)oxaziridines in THF afforded α-hydroxyester with 53-73percent ee, but the product from the solid state reactions was racemic.The results suggest that the enolate exists and reacts as an aggregate in the solid state reactions.