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.
- 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. 2013, 78, 2500 [View Journal Page]
- 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]