Stereoselective Synthesis of Polypropionate Units and Heterocyclic Compounds by Cyclopropylcarbinol Ring-Opening with Mercury(II) Salts

The mercury(II)-mediated electrophilic ring-opening reaction of various cyclopropylcarbinol derivatives bearing adjacent stereocenters and a remote nucleophilic functional group provides a useful strategy for synthesizing compounds bearing several contiguous stereocenters. These highly diastereoselective reactions occur with anchimeric assistance by the internal nucleophilic moiety and afford synthetically valuable building blocks such as polypropionate units or heterocyclic compounds. The application of cyclopropylcarbinol ring-opening for the preparation of functionalized oxygen heterocycles in natural product synthesis is also outlined.