Catalytic Site‐, Diastereo‐, and Enantioselective Cascade Iodocyclization of 2‐Geranylarenols

Abstract

AbstractA chiral amidophosphate‐N‐iodosuccinimide cooperative catalysis has been developed for the site‐, diastereo‐, and enantioselective iodocyclization of 2‐geranylarenols with molecular iodine to give the corresponding iodo‐containing polycyclic compounds with good levels of selectivity. This is the first example of a catalytic enantioselective iodocarbocyclization. A reactive chiral iodonium species is generated from molecular iodine via the dual halogen‐bonding interactions with a chiral Lewis base and Lewis acid. The sterically demanding 3,3′‐substituents of the chiral BINOL‐derived amidophosphate are critical to induce the site‐selective iodination at the less‐hindered terminal alkenyl moiety of 2‐geranylarenols.