The Shapiro as well as the Bamford-Stevens reactions are very convenient methods for preparing numerous olefinic compounds from ketones and aldehydes via sulfonylhydrazones. These reactions allow preparation not only simple molecules with a double bond but also larger, complex systems that could have biological activity. Therefore, the synthetical aspects of above-mentioned reactions are of broad interest to organic chemists. This mini review describes the application of Shapiro as well as Bamford-Stevens reactions in the preparation of olefinic compounds.
Peptidomimetics are molecules related to natural peptides that have an artificial unit incorporated in their structure. Such structural modifications, mimicking properties of natural amino acids, can be responsible for differently pronounced activity. Among others, amino acid derivatives with fluorinated olefinic motifies can act as building blocks in the synthesis of complex molecules with potential biological activity. Therefore, the synthetic approaches to the fluorinated olefinic moiety amino acids are of interest to organic chemists. There are different synthetic methods yielding fluorinated olefins having significant value in the synthesis of amino acid derivatives. This mini review describes the latest achievements in the synthesis of amino acids bearing mono-, di-or trifluorovinyl moiety.
Herein, we report the synthesis of analogues of amino acids with a monofluorovinyl moiety. Interestingly, we have found that cyclization of the obtained products proceeds easily in all cases. The cyclization process has not previously been observed at this reaction stage, and such fluorinated lactams derived from phenylalanine, valine, alanine have not been described before.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.