title: Ruthenium-catalyzed asymmetric [2 + 2] cycloadditions between chiral acyl camphorsultam-substituted alkynes and bicyclic alkenes.
abstract: Ruthenium-catalyzed asymmetric [2 + 2] cycloadditions between chiral acyl camphorsultam-functionalized alkynes and bicyclic alkenes were examined, providing adducts with complete exo stereoselectivity in good overall yield and enantioselectivity (up to 99% and 166:1, respectively), as well as appreciable diastereoselectivity (up to 163:1). The diastereoselectivity showed dependence on the solvent and temperature, as well as on the substitution pattern of the reacting alkyne and bicyclic alkene components. In general, higher diastereoselectivities were observed for reactions conducted in ethereal solvents and at lower temperatures between N-propynoyl camphorsultams and bicyclic alkenes.
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph , Guelph, Ontario Canada N1G 2W1.
authors.forename: Jordan
authors.initials: J
authors.lastname: Goodreid
authors.forename: Karine
authors.initials: K
authors.lastname: Villeneuve
authors.forename: Emily
authors.initials: E
authors.lastname: Carlson
authors.forename: William
authors.initials: W
authors.lastname: Tam
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D006575:Heterocyclic Compounds, 3-Ring; C000596000:camphorsultam; D012428:Ruthenium