Ruthenium-catalyzed nucleophilic ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols.
Ruthenium-catalyzed nucleophilic ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols were investigated. When a neutral ruthenium(II) catalyst, Cp*RuCl(COD), was used in MeOH, the trans-1,2-ring opened product was formed as the only regio- and stereoisomer. On the other hand, when a cationic ruthenium(II) catalyst, [CpRu(CH(3)CN)(3)]PF(6), was used in MeOH, the cis-1,2-ring opened product was formed exclusively. Moderate to excellent stereoselectivity (70:30 to 100:0) was observed with various alcohols.
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.
Ben P
BP
Machin
Jennifer
J
Howell
Jérémie
J
Mandel
Nicolas
N
Blanchard
William
W
Tam
D000438:Alcohols / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
C540994:3-aza-2-oxabicyclo(2.2.1)hept-5-ene; D000438:Alcohols; D019086:Bridged Bicyclo Compounds, Heterocyclic; D012428:Ruthenium