Chiral Hypervalent Iodine(III) Catalyzed Enantioselective Diacetoxylation of Styrenes

Muñiz and Ishihara et al. have reported the enantioselective diacetoxylation of styrene derivatives using chiral hypervalent iodine catalysts. According to their report, a chiral hypervalent iodine compound (1) is in situ prepared from (R,R)-2-iodo-1,3-bis[1-(mesitylcarbamoyl)ethoxy]benzene and peracetic acid, and used as a chiral catalyst for the enantioselective dioxygenation of styrene leading to the corresponding vicinal diacetoxylation product. In this reaction, the amide groups of the chiral catalyst 1 engage in intramolecular hydrogen bonding with the acetoxy groups at the iodine(III) center to force the formation of ideal asymmetric environment which plays a significant role in the enantioselective intermolecular reaction.