Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes.

Abstract

The first [4 + 2] cyclization of para-quinone methide (p-QM) derivatives with allenes has been established via phosphine catalysis, which afforded a series of chroman derivatives in high yields (up to 97%) and excellent (E/Z)-selectivities (all >95 : 5 E/Z). This reaction will not only enrich the research contents of cyclization reactions involving p-QM derivatives, but also provide a good example of the application of allenes and phosphine catalysis in cyclization reactions. In addition, this approach also offers a useful method for the construction of chroman scaffolds.