Pd-Catalyzed Asymmetric Three-Component Allenol Carbopalladation and Allylic Cycloaddition Cascade: A Route to Functionalized Tetrahydrofurans

The first Pd-catalyzed asymmetric three-component reaction of 2,3-allenol, aryl iodides, and 2-arylmethylenemolononitriles has been developed via an allenol carbopalladation and an allylic cycloaddition cascade. This process allows rapid access to substituted tetrahydrofurans bearing diverse functional groups in good yields with high diastereoselectivities and excellent enantioselectivities. The concise total synthesis of a lignan, (-)-2-episesaminone, has been achieved by the elaboration of a functionalized tetrahydrofuran obtained from this reaction.

Automated summary

The first Pd-catalyzed asymmetric three-component reaction of 2,3-allenol, aryl iodides, and 2-arylmethylenemolononitriles has been developed, allowing rapid access to substituted tetrahydrofurans with diverse functional groups in good yields and high selectivities. The concise total synthesis of a lignan, (-)-2-episesaminone, has been achieved using a functionalized tetrahydrofuran obtained from this reaction.