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.