Novel DABCO-Catalyzed Regio-and Diastereoselective Nucleophilic Substitution of Baylis-HillmanAcetates with TosMIC

An efficient DABCO-mediated regio- and diastereoselective substitution of Baylis-Hillman acetates with p-toluenesulfonylmethyl isocyanide (TosMIC) has been developed via a tandem S N 2'-S N 2' mechanism. The products were obtained in excellent yields (80-92%) and in moderate diastereoselectivity (66-80%).