Enantioselective synthesis of [7]helicene: dramatic effects of olefin additives and aromatic solvents in asymmetric olefin metathesis.
The asymmetric synthesis of [7]helicene was accomplished in good ee (80%) by kinetic resolution by means of asymmetric olefin metathesis. Three key factors contributed to the success of the kinetic resolution: the use of new Ru-based olefin metathesis catalysts bearing C1-symmetric N-heterocyclic carbene ligands, simple olefins as additives to control the nature of the propagating alkylidene and hexafluorobenzene as a solvent.
Grandbois
Alain
A
Department of Chemistry, Université de Montréal, C.P. 6128 Station Downtown, Montréal, Québec, H3C 3J7, Canada.
Collins
Shawn K
SK
D000475:Alkenes / Q000737:chemistry*; D005466:Fluorocarbons / Q000737:chemistry; D007700:Kinetics; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D005466:Fluorocarbons; D011083:Polycyclic Compounds; D012997:Solvents; C031660:helicenes; C003005:hexafluorobenzene