Palladium-Catalyzed Reaction of 2,3-Allenols with Amines: Synthesis of [3]Dendralenes and 1,3-Dienes Containing Allylic Amino and Hydroxy Groups

Palladium-catalyzed reaction of 2,3-allenols with amines was carried out to construct conjugated polyenes with allylic amino and hydroxy groups. [Pd(pi-allyl)Cl](2)/P(2-furyl)(3)-catalyzed reaction in MeOH led to (Z)-configurated [3]dendralene derivatives and Pd(OAc)(2)/P(2-furyl)(3)-catalyzed reaction in iPrOH resulted in (1Z,3E)-1,3-diene derivatives.

Automated summary

Conjugated polyenes with allylic amino and hydroxy groups were successfully synthesized through the palladium-catalyzed reaction of 2,3-allenols with amines. Using MeOH as the solvent led to (Z)-configured [3]dendralene derivatives, while using iPrOH as the solvent resulted in (1Z,3E)-1,3-diene derivatives.