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. Parent and P. Deslongchamps, Org. Biomol. Chem., 2016, 14, 11183 DOI: 10.1039/C6OB02263D
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