Aziridinium Rearrangements

A recent research programme has exploited aziridinium intermediates in the syntheses of β-fluoro-α-amino acids, β-hydroxy-α-amino acids and tetrahydro-isoquinolines from common α-hydroxy-β-amino ester precursors. In each case, activation of the α-hydroxyl group as a leaving group is followed by attack of the β-amino substituent to give an aziridinium ion in the key rearrangement step.
 

Key Publications: 

  1. Trading N and O. Part 3: Synthesis of 1,2,3,4-tetrahydroisoquinolines from α-hydroxy-β-amino esters
    Davies, S. G.; Fletcher, A. M.; Frost, A. B.; Kennedy, M. S.; Roberts, P. M.; Thomson,
    J. E. Tetrahedron 201672, 2139 [View Journal Page]
  2. Asymmetric synthesis of substituted anti-β-fluorophenylalanines
    Davies, S. G.; Fletcher, A. M.; Frost, A. B.; Roberts, P. M.; Thomson, J. E. Org. Lett. 201517, 2254
    [View Journal Page]
  3. Trading and O. Part 2: Exploiting aziridinium intermediates for the synthesis of
    β-hydroxy-α-amino acids
    Davies, S. G.; Fletcher, A. M.; Frost, A. B.; Roberts, P. M.; Thomson, J. E. Tetrahedron 201470, 5849
    [View Journal Page]

 

 

 

 

 

 

 

 


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