Memory of Chirality (MOC) in Intramolecular sp³ C–H Amination

Abstract

‘Memory of chirality’ (MOC) is an important concept for the development of efficient asymmetric transformations. However, the phenomenon of MOC in C–H functionalization is still rare. In the past decades, three types of intramolecular C–H amination involving C–H insertion of metal nitrenoids, 1-aza-2-azoniaallene salts, and benzamides to construct N-heterocyclic compounds have been developed in Du Bois, Brewer, and our group, respectively. In these reactions, the formation of a C–N bond does not result in the loss of stereochemical information at the stereogenic center. Here, we discuss the scope, mechanism, and application of these transformations and provide a perspective on the development of this field in future.

Key words

memory of chirality - asymmetric synthesis - N-hetero­cycles - amination - C–H functionalization

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