Journal
TETRAHEDRON-ASYMMETRY
Volume 16, Issue 9, Pages 1583-1594Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2005.02.014
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Optically active protected sulfamidate 2-phosphonates have been synthesized from either (R)- or (S)-N-benzyl-2-phosphonoserine for use as chiral synthons. These sulfamidates have been shown to undergo nucleophilic substitution with select nucleophiles, to afford following N-sulfate removal, the beta-substituted alpha-amino-2-phosphonates. N-Sulfate removal was accomplished using boron trifluoride etherate in the presence of either n-propylthiol or N-hydroxysuccinimide allowing retention of the diethylphosphonate ester groups. Replacement of the unpleasant smelling n-propylthiol with N-hydroxysucinimide provides higher yields of the desired products. Synthesis of P-S-substituted analogues required the use of cesium carbonate as a base. The sulfamidates described have excellent stability and have been demonstrated, using chiral HPLC, to be greater than 97% enantiomerically pure. (C) 2005 Elsevier Ltd. All rights reserved.
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