Ireland-Claisen Rearrangements

Asymmetric syntheses of C(5)-substituted transpentacins were achieved in nine steps from commercially available starting materials via the Ireland-Claisen rearrangement of two enantiopure β-amino allyl esters, followed by ring-closing metathesis, reduction and deprotection.


Key Recent Publications: 

  1. Diastereoselective Ireland–Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins
    Davies, S. G; Fletcher, A. M.; Lee, J. A; Roberts, P. M.; Souleymanou, M. Y.; Thomson, J. E.; Zammit, C. M.
    Org. Biomol. Chem. 201412, 2702 [View Journal Page]
  2. Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via diastereselective Ireland-Claisen rearrangements
    Davies, S. G.; Fletcher, A. M.; Roberts, P. M.; Thomson, J. E.; Zammit, C. M. Chem. Commun. 201349, 7037 [View Journal Page]










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