Highly efficient deprotection of N-p-toluenesulfinyl group of β- branched Baylis-Hillman adducts by using amberlite IR-120 (plus) ion-exchange resin

An efficient deprotection of N-p-toluenesulfinyl group of β-branched Baylis-Hillman adducts has been developed by using Amberlite IR-120 (plus) ion-exchange resin in methanol solution at room temperature. Good to quantitative yields have been obtained for six examples. No racemization was detected under the mild conditions. This new method provides a simultaneous deprotection/purification, which has the great advantage over the solution phase deprotection technique of simplicity of work-up. (C) 2000 Elsevier Science Ltd.