Abstract
AbstractWe have described the chemoselective behavior of iodine in the oxidative esterification and electrophilic iodocyclization of hydroxyalkynyl aldehydes that contain a primary alcohol moiety. In the presence of an alcohol, which serves as the nucleophile and solvent, the reaction of the hydroxyalkynyl aldehydes and I2 proceeds through a hemiacetal species to give alkyl 4‐(3‐hydroxyalkynyl)benzoate esters. In CH2Cl2, these substrates undergo an electrophilic iodocyclization through a cyclic iodonium ion to provide a synthetic route for the formation of the bioactive dihydrofuran/pyran ring system.
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