4.02 Nucleophilic Addition-Electrophilic Coupling with a Carbanion Intermediate

Abstract

The strategy of nucleophilic addition–electrophilic couplings has become one of the central tenets and instruments in the arsenal of modern organic synthesis, since the discovery and development of novel catalytic systems and activation modes. In addition to traditional metal catalysis, organocatalysis has emerged as a new complementary tool, which has made significant achievements in the field. The broad selection of α,β-unsaturated compounds including α,β-unsaturated aldehydes, ketones, esters, amides, nitroolefins, and alkynals is presented, together with a variety of Michael donors and carbophilic electrophiles have been conceived and harvested for the efficient and stereoselective construction of complex molecular architectures, which usually possess at least two chiral centers. The approach can dramatically improve the synthetic efficiency in a fashion of the atom economy, and naturally falls into the category of a cascade reaction.