Decoding the ‘black box’ reactivity that is organocuprate conjugate addition chemistry

Abstract

Understanding of the 1,4-addition of organocuprates, especially LiCuR₂ species, to enone Michael acceptors has blossomed in the light of recent kinetic, NMR, and theoretical investigations. These investigations have been reviewed and are compared to the various reaction co-ordinates they support. Emphasis is placed on relating the theoretical calculations to physical data extracted from real systems. The mechanism of cuprate conjugate addition is compared to related reactions including: additions to ynones, alkene carbocupration, and S_N2′ allylic and propargylic substitution reactions.