A tandem Prins/Friedel-Crafts cascade strategy has been developed for the synthesis of hexahydro-2Hbenzo[g]chromene derivatives. Under action of equimolecular amount of BF 3 etherate, δ,ε-unsaturated alcohols and arylacetaldehydes are coupled to form oxocarbenium ion intermediates, which are captured by the alkene moiety through a favored six-membered transition state. The Prins-cyclization resultant tertiary carbenium ions undergo consecutive intra-molecular Friedel-Crafts cyclization to create the tricyclic products. This process enables a tandem formation of three new chemical bonds in one single operation with high yields and stereoselectivity in most cases. When cyclic substituents are involved, a variety of spiro derivatives could also be synthesized successfully, which further proved the robustness of this methodology.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.