Memory of chirality: An emerging strategy for asymmetric synthesis

'Memory of chirality' (MOC) is an intriguing strategy for asymmetric synthesis because it appears to do the impossible: the sole chiral center of a molecule directs the stereochemical course of a reaction even though that center is destroyed in the key reactive intermediate. This review describes the critical role of transient conformational chirality in these processes, and defines the three essential requirements for success in an MOC method. The growing application of MOC to asymmetric synthesis methodology is discussed, with extensive coverage of enolate, radical, photochemical and carbocation reactions.EI011-1