Desymmetrization

[1] According to IUPAC, desymmetrization involves the "... the conversion of a prochiral molecular entity into a chiral one.

"[2] Typical substrates are epoxides, diols, dienes, and cyclic carboxylic acid anhydrides.

[3] In another example, a symmetrical cyclic imide is subjected to asymmetric deprotonation resulting in a chiral product with high enantioselectivity.

[4] Partial hydrogenation]] converts benzil (PhC(O)C(O)Ph) into chiral hydrobenzoin.

The alcoholysis of cyclic anhydrides can be conducted enantiosymmetrically using chiral amine catalysts.