Enantiorecognition Phenomena

Enantioselective molecular recognition phenomena are of extreme importance to the fields of both chemistry and biology. Synthetic chemists can contribute to the understanding of this arena through the development of novel kinetic, dynamic kinetic and parallel kinetic resolution protocols, or through the application of double asymmetric induction. The efficient kinetic and parallel kinetic resolutions of a range of 3- and 5-substituted cyclopent-1-ene-carboxylates, utilising the conjugate addition of either homochiral or a pseudoenantiomeric mixture of homochiral lithium amides, respectively, has been developed by us as an expedient route to enantiopure 3- and 5-substituted analogues of the antifungal agents cispentacin and transpentacin, which are also useful β-amino acids for the construction of β-peptides.
 

 Parallel kinetic resolution
 

Key Publications:

  1. Parallel kinetic resolution of acyclic γ-amino-α,β-unsaturated esters: application to the asymmetric synthesis of 4-aminopyrrolidin-2-ones
    Davies, S. G.; Lee, J. A.; Roberts, P. M.; Thomson, J. E.; Yin, J. Org. Lett. 201214, 218
    [View Journal Page]
  2. Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin and transhexacin derivatives
    Davies, S. G.; Durbin, M. J.; Hartman, S. J. S.; Matsuno, A.; Roberts, P. M.; Russell, A. J.; Smith, A. D.; Thomson, J. E.; Toms, S. M. Tetrahedron: Asymmetry 2008, 19, 2870 [View Journal Page]
  3. Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates
    Bull, S. D.; Davies, S. G.; Epstein, S. W.; Garner, A. C.; Mujtaba, N.; Roberts, P. M.; Savory, E. D.; Smith, A. D.; Tamayo, J. A.; Watkin, D. J. Tetrahedron 2006, 62, 7911 [View Journal Page]
  4. Kinetic resolution and parallel kinetic resolution of methyl (±)-5-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 5-alkyl-cispentacin derivatives
    Davies, S. G.; Garner, A. C.; Long, M. J. C.; Morrison, R. M.; Roberts, P. M.; Smith, A. D.; Sweet, M. J.; Withey, J. M. Org. Biomol. Chem. 2005, 3, 2762 [View Journal Page]
  5. Parallel kinetic resolution of tert-butyl (RS)-3-alkylcyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkylcispentacin derivatives
    Davies, S. G; Garner, A. C.; Long, M. J. C.; Smith, A. D.; Sweet, M. J.; Withey, J. M. Org. Biomol. Chem. 2004, 2, 3355 [View Journal Page]

 

 

 

 

 


Site Map | Printable View | © 2008 - 2017 Department of Chemistry - University of Oxford

Powered by mojoPortal | HTML 5 | CSS | Design by styleshout