Unprecedented Reactivity in Nucleophilic Ring Opening of Oxabicycles

Significance

The authors report novel reactivity for oxabicyclo[2.2.1]heptenes and -heptanes where nucleophilic attack occurs at the bridge-head position to yield heterocyclic structures in a stereospecific manner. When this methodology is combined with stereoselective methods available for making the precursor oxabicycles the result is a powerful method for making stereochemically rich heterocycles.