Bent Bonds and the Antiperiplanar Hypothesis and the Reactivity at the Anomeric Center in Pyranosides
A solo contribution from the P. Deslongchamps group.
The stereoselectivity of nucleophilic addition on oxocarbenium ions derived from the bicyclic pyranoside model with or without a C2–OR group can be understood through the use of the bent-bond and the antiperiplanar hypothesis in conjunction with the concept of hyperconjugation as an alternative interpretive model of structure and reactivity.
J.-F. Parent, P. Deslongchamps, Bent Bonds and the Antiperiplanar Hypothesis and the Reactivity at the Anomeric Center in Pyranosides. Org. Biomol. Chem., 2016, 14, 11183-11198.