Synthesis and Reactivity of Bicyclo[3.2.1]octanoid-Derived Cyclopropanes

Photochemical oxa-di-pi-methane rearrangement of bicyclo[3.2.1]octanoid scaffolds affords multifunctional, donor acceptor cyclopropanes. A related photochemical reaction of an iminium ether substrate uncovered an unprecedented aza-di-pi-methane rearrangement of a beta,gamma-unsaturated iminium. Donor acceptor cyclopropanes have been evaluated as substrates for reactions generating several new chemotypes.