[3 + 2]-Annulation of Azaoxyallyl Cations and Thiocarbonyls for the Assembly of Thiazolidin-4-ones

Abstract

A base-promoted, efficient [3 + 2] annulation between azaoxyallyl cations and thiocarbonyls is reported for flexible access to highly functionalized thiazolidin-4-one derivatives in good to excellent yields. An intriguing feature of this method is the metal or Lewis acid free late-stage entry of distinct set of functional groups at C2 of thiazolidin-4-ones via substitution of a latent amino functional group. Overall, this approach constitutes a general platform for convenient access to this medicinally important scaffold.