An efficient approach to the synthesis of enantiomerically pure trans-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids |
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Authors: | Katarzyna Wąsek Jacek Kędzia Henryk Krawczyk |
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Institution: | Institute of Organic Chemistry, Technical University (Politechnika), 90-924 ?ód?, ?eromskiego 116, Poland |
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Abstract: | The synthesis of (1R,2S)- and (1S,2R)-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids was accomplished using different strategies. The (1R,2S)-stereoisomer could be efficiently obtained by the cyclopropanation of ethyl diethoxyphosphorylacetate with the cyclic sulfate derived from (S)-3-benzyloxy-1,2-propandiol as a key step. The (1S,2R)-stereoisomer was synthesized from a readily available (1S,5R)-3-oxabicyclo3.1.0]hexan-2-on-1-phosphonate. |
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