title: 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.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Hall, Notre Dame, Indiana 46556, USA.
authors.forename: Baiyuan
authors.initials: B
authors.lastname: Yang
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C540994:3-aza-2-oxabicyclo(2.2.1)hept-5-ene; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D008698:Mesylates; C012077:trifluoromethanesulfonic acid