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Indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems with alcohols and water were investigated. Reactions of [2.2.1] bicyclic systems gave anti-1,2-, anti-1,4- and syn-1,4-ring-opened products with moderate to excellent regio- and stereoselectivity. When [2.2.2] bicyclic systems were subjected to similar reaction conditions, only anti-1,2 and anti-1,4-ring-opened products were obtained.

journal of organic chemistry

Regio- and Stereoselective Indium Triflate-Mediated Nucleophilic Ring-Opening Reactions of 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene Systems