Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 11-12, Pages 1826-1832Publisher
WILEY-BLACKWELL
DOI: 10.1002/adsc.200900269
Keywords
asymmetric catalysis; desymmetrization; N-heterocyclic carbenes; olefin metathesis
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Funding
- NSERC (Canada)
- FQRNT (Quebec)
- CFI (Canada)
- Boehringer higelheim (Canada) Ltd
- Merck Frosst Centre for Therapeutic Research
- Universite de Montreal
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Four new ruthenium-based olefin metathesis catalysts that possess an N-heterocyclic carbene (NHC) ligand with benzyl (Bn) or or n-propyl (n-Pr) N-alkyl groups have been prepared. The synthetic routes developed for the synthesis of the required di-hydroimidazolium salts are general. Catalysts bearing larger NHC ligands with larger N-alkyl groups displayed improved thermal and solution state stability up to 80 degrees C. The reactivity of the new catalysts in ring-closing metathesis is directly related to the increased steric bulk of the NHC ligand. The new catalysts have been evaluated in desymmetrization reactions and the nature of the N-alkyl group of the NHC ligands has been shown to have an important effect on the observed enantioselectivities.
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