Iodocyclization of O-(3-Cyclohexenyl)thiocarbamidates. An Unexpected Approach to Vicinal cis-Aminocyclohexenols

An unprecedented and unexpected iodocyclization of O-(3-cyclohexenyl)thiocarbamidates 2a−c to diiodides 7a−c, followed by alkaline hydrolysis and iodide elimination, has uncovered an alternative approach to vicinal cis-aminocyclohexenols 10a−c and 11a−c. This represents a new approach to these interesting building blocks.