ω‐Alkenylallylboronates: Design, Synthesis, and Application to the Asymmetric Allylation/RCM Tandem Sequence

Abstract

AbstractThe synthesis of allylboronates bearing an alkenyl moiety appended at a remote position is described for the first time. For that aim, the palladium‐catalyzed borylation of the corresponding allylic alcohols was used as the key step. The required allylic alcohols were in turn obtained in 3–4 step sequences. The presence of an extra alkenyl moiety at a strategic position allows the triggering of a tandem asymmetric allylation/RCM reaction sequence that efficiently affords different sized cycles featuring two consecutive stereocenters and an exocyclic alcohol function. Products are obtained in moderate to excellent yields and high enantioselectivities, in most of the cases.