(Hydroxyimino)Phosphonoacetic Acids: Synthesis,Stereochemistry and Reactivity |
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Authors: | Charles E. McKenna Boris A. Kashemirov Mari Fujimolo |
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Affiliation: | Department of Chemistry , University of Southern California , Los Angeles, CA, 90089-0744, USA |
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Abstract: | Abstract Individual E/Z isomers of the C-methyl ester 1 of α-(hydroxyimino)phosphonoacetic acid (“troika acid”) were recently prepared as dicyclohexylammonium salts and found to be stable at neutral pH.1 On alkaline demethylation followed by pH adjustment to 6–7, E?1 and Z?1 stereospecifically undergo P-Cαand Cα-Cβ cleavage, respectively.1 Herein we report synthesis of the corresponding P-methyl ester from trimethyl phos-phonoacetate 2. The product was isolated as its bis-DCHA+ salt E-3, with stereochemistry assigned by NMR.2 |
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