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Abstract | Cited by

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.

Graphical abstract: Bent bonds (τ) and the antiperiplanar hypothesis, and the reactivity at the anomeric center in pyranosides

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