Diastereodivergent Osmylation

Dihydroxylation of acyclic allylic amines under either Upjohn conditions (OsO4/NMO) or Donohoe conditions (OsO4/TMEDA) proceeds with remarkably high and antipodal diastereofacial selectivity to give diastereoisomeric 2,4,5-trihydroxy-3-aminoesters. These highly functionalised amino triols have been elaborated to the corresponding aminosugars, such as 3,6-dideoxy-3-amino-L-talose.

Diastereodivergent osmylation

Key Publications:

  1. Asymmetric syntheses of APTO and AETD: the β-amino acid fragments within microsclerodermins 
    C, D and E
    Davies, S. G.; Fletcher, A. M; Foster, E. M; Lee, J. A; Roberts, P. M.; Thomson, J. E. J. Org. Chem. 201378, 2500 [View Journal Page]
  2. Highly diastereoselective and stereodivergent dihydroxylations of acyclic allylic amines: application to the asymmetric synthesis of 3,6-dideoxy-3-amino-L-talose
    Csatayová, K.; Davies, S. G.; Lee, J. A.; Roberts, P. M.; Russell, A. J.; Thomson, J. E.; Wilson, D. L. Org. Lett. 2011, 13, 2606 [View Journal Page]







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