Diastereoselective Three-Component 1,3-Dipolar Cycloaddition to Access Functionalized <i>β</i>-Tetrahydrocarboline- and Tetrahydroisoquinoline-Fused Spirooxindoles

Abstract

A chemselective catalyst-free three-component 1,3-dipolar cycloaddition has been described. The unique polycyclic THPI and THIQs were creatively employed as dipolarophiles, which led to the formation of functionalized β-tetrahydrocarboline- and tetrahydroisoquinoline-fused spirooxindoles in 60–94% of yields with excellent diastereoselectivities (10: 1−>99: 1 dr). This reaction not only realizes a concise THPI- or THIQs-based 1,3-dipolar cycloaddition, but also provides a practical strategy for the construction of two distinctive spirooxindole skeletons.

Keywords

• three component
• 1,3-dipolar cycloaddition
• dipolarophiles
• fused spirooxindoles
• chemoselectivity