Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: catalyst and substrate studies leading to a mechanistic working model.
basic_science · Level V
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Abstract
Catalyst and substrate studies have been performed on the rhodium-catalyzed asymmetric ring opening reaction. A working model is advanced that involves oxidative insertion with retention to form an organorhodium intermediate that then undergoes nucleophilic attack with inversion. Kinetic and competition experiments have uncovered evidence for a proton transfer step in the catalytic cycle that may activate both the allylrhodium intermediate and the nucleophile. We have also conducted experiments designed to understand which properties of the PPF-P(t)Bu(2) ligand contribute to the high reactivities and enantioselectivities.