Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 30, Pages 9323-9329Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801033
Keywords
asymmetric synthesis; catalysis; helicenes; kinetic resolution; olefin metathesis
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Funding
- NSERC (Canada)
- FQRNT (Quebec)
- CFI (Canada)
- Boehringer Ingelheim (Canada) Ltd
- Merck Frosst Centre for Therapeutic Research
- Universite de Montreal
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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 Cl-symmetric N-heterocyclic carbene ligands, simple olefins as additives to control the nature of the propagating alkylidene and hexafluorobenzene as a solvent.
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