Hydroxylated amino acid synthesis

The sense of diastereoselectivity in the epoxidation of 1-arylthio-1-nitroalkenes can be controlled simply by choice of the epoxidising agent. The diastereo- and enantiomerically pure epoxides can be converted into alpha-amino acids by treatment with ammonia.

Synthesis of hydroxylated amino acids

Key References

Richard F.W. Jackson, Nicholas J. Palmer, Martin J. Wythes, William Clegg, and Mark R.J. Elsegood, J. Org. Chem., 1995, 60, 6431-6440.

Z.M. Adams, R.F.W. Jackson, N.J. Palmer, H.K. Rami, and M.J. Wythes, J. Chem. Soc., Perkin Trans. 1, 1999, 937-948.

E. Dumez, A. Szeki and R.F.W. Jackson, Synlett, 2001, 1214-1216.

L. Ambroise, E. Dumez, A. Szeki and R.F.W. Jackson, Synthesis, 2002, 2296-2308.