Zhang Wei, Lu Yimin
Fluorous Technologies, Inc., University of Pittsburgh Applied Research Center, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA.
Org Lett. 2003 Jul 10;5(14):2555-8. doi: 10.1021/ol034854a.
[reaction: see text] A fluorous synthesis of hydantoins is introduced. The reaction of perfluoroalkyl (Rfh)-tagged amino esters with an isocyanate is followed by the cyclization of ureas and simultaneous cleavage of the fluorous tag to afford hydantoins. The product purification is performed by solid-phase extraction over FluoroFlash cartridges, and no fluorous solvent is involved in either the reaction or the separation processes. The same method applies to synthesis of thiohydantoins.