Tandem Iodocyclization of 1,5-Enynes

Abstract

Tandem reaction where multiple bonds are formed in a stereocontrolled manner in a single operation represents a highly desirable goal in view of the increasing complexity of natural products. In this respect, electrophile-induced cyclization of alkenes and alkynes has been the subject of intense study. Particularly, iodo-N,O-functionalization, such as iodolactonization has been amply successful in the context of complex molecule synthesis. However, little attention have been paid to the tandem version of this classical reaction. Herein, we report that 1,5-enyne serves as an effective platform to induce iodonium-initiated tandem C-C and C-O bond formation and disclose a novel pathway toward a highly functionalized iodocycloalkenes with multiple stereocenters.