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Enantioselective Synthesis of [7]Helicene: Dramatic Effects of Olefin Additives and Aromatic Solvents in Asymmetric Olefin Metathesis
Author(s) -
Grandbois Alain,
Collins Shawn K.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801033
Subject(s) - helicene , enantioselective synthesis , kinetic resolution , olefin fiber , olefin metathesis , chemistry , ring opening metathesis polymerisation , acyclic diene metathesis , metathesis , organic chemistry , carbene , catalysis , molecule , polymerization , polymer
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 C 1 ‐symmetric N‐heterocyclic carbene ligands, simple olefins as additives to control the nature of the propagating alkylidene and hexafluorobenzene as a solvent.