Poster Presentation 5th Modern Solid Phase Peptide Synthesis Symposium 2015

Synthesis and application of a family of specialist olefin metathesis catalysts (#57)

Ellen C. Gleeson 1 , Zhen J. Wang 1 , W. Roy Jackson 1 , Andrea Robinson 1
  1. School of Chemistry, Monash University, Clayton, VIC, Australia

There is a demand for specialist olefin metathesis catalysts to address specific synthetic needs such as activity in highly polar solvents and solvent-free conditions, and removal of Ru-residue from the reaction mixture.1 Numerous catalysts have been designed to address these challenges, although their development has had a narrow focus towards one specific property.2 As part of our study on the improvement of olefin metathesis technology,3 we recently investigated a divergent strategy which allows the preparation of a family of functionalised Ru-alkylidene based catalysts. Beginning with a common ligand precursor derived from commercially available L‑tyrosine, catalyst analogues with a range of different properties can be synthesised.4 Peptide supports can be used to generate a recyclable catalyst with the potential to moderate reactivity and selectivity via neighbouring group effects provided by the sequence.

  1. Vougiokalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746.
  2. a) Buchmeiser, M. R. Chem. Rev. 2009, 15, 2317; b) Tomasek, J.; Schaltz, J. Green Chem. 2013, 15, 2317.
  3. a) Wang, Z. J.; Jackson, W. R.; Robinson, A. J. Org. Lett. 2013, 15, 3006; b) Woodward, C. P.; Spiccia, N. D.; Jackson, W. R.; Robinson, A. J. Chem. Commun. 2011, 47, 779.
  4. Gleeson, E. C.; Wang, Z. J.; Jackson, W. R.; Robinson, A. J. J. Org. Chem., 2015, 80, 7205.