The availability of methods for the introduction of the pentafluorosulfanyl group into carboxylic acids has enabled the synthesis of pentafluorosulfanyl analogs of alanine and valine.  The synthesis of these new materials from ethyl pyruvate and ethyl 2-oxobutanoate is described.  With the new molecules in hand, it has been possible to examine in more detail the influence of the SF5 group on the conformation and reactivity of those substances.  The steric, electronic and dipolar effects of substitution will be described.

Synthesis of pentafluorosulfanyl analogs of valine and alanine

244th National Meeting (2012)

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