Making and breaking C-C bonds: Development of enantioselective Diels-Alder and oxidative cleavage reactions

A chiral cationic oxazaborolidine catalyst was used in the development of the first asymmetric and regioselective Diels-Alder reaction of substituted cyclopentadienes as well as the first enantioselective Diels-Alder reaction of acetylenic ketones with cyclic and acyclic dienes. Furthermore, addition of nitrosobenzene to the anions of various carbonyl compounds provides a novel carbon-carbon bond oxidative cleavage methodology. The newly developed Diels-Alder reaction of substituted cyclopentadienes and oxidative cleavage reactions were applied in the formal total synthesis of Platensimycin.