Synthesis of Thio-/Selenopyrrolines via SnCl4-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor cyclopropanes with Thio-/Selenocyanates

Abstract

A straightforward protocol has been developed to access thio-/ selenopyrrolines through a (3+2)-cycloaddition of aryl thio-/ selenocyanates with donor-acceptor cyclopropanes (DACs) in the presence of SnCl4 as a Lewis acid catalyst. Further, good chemoselectivity was observed when DACs were treated with 3-cyano phenyl thiocyanate. These results suggest that thiocyanate is more reactive than nitrile moiety in such (3+2)- cycloaddition reactions.