Studies on the Enantioselectivity in Bu4N-Catalyzed Nucleophilic Substitution of Optically Active Allylic Carbonates with Malonate

Article abstract of DOI:10.1021/jo00253a049

The stereochemical outcomes of optically active allylic carbonates 2, 5, and 9 with malonate in the presence of iron catalyst 1 were determined.It was found that in every case the nucleophile predominantly attacked at the carbon atom where the leaving group was attached, and the corresponding prevailing regioisomer 3, 6, or 10 was obtained with high retention of configuration at the chiral center.