Palladium‐Catalyzed Diastereoselective Synthesis of (Z)‐Conjugated Enynyl Homoallylic Alcohols

Abstract

The diastereoselective synthesis of antihomoallylic alcohols bearing conjugated (Z)-enynes through a palladium-catalyzed three-component reaction is described. This reaction features a broad substrate scope, good functional group compatibility, and high levels of (Z)-alkene stereocontrol. In this reaction, Pd(0) functions as a catalyst in two fundamental steps of the tandem sequence: 1) the generation of a borylated π-allylpalladium species from bifunctional conjunctive reagents, inducing umpolung allylation of aldehydes, and 2) C(sp 2 )À C-(sp) cross-coupling. Further transformations of the obtained products highlight their synthetic utility.

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

“…A recent example of complex multicomponent synthesis was described by Horino and co-workers [ 188 ]. In the reaction ( Scheme 12 ), the authors observed high levels of ( Z )-alkene stereocontrol.…”