Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Michael Additions Involving Amino Acid Esters with Alkenyl N-Heterocycles

Michael Additions Involving Amino Acid Esters with Alkenyl N-Heterocycles
Douglas A. Klumpp, Sean H. Kennedy
Michael addition has been achieved with a variety of amino acid esters and 2- or 4-vinylpyridine. Similar reactions were accomplished with an alkenyl-substituted pyrimidine, pyrazine, thiazole, quinoxaline, benzoxazole, and quinolone. In reactions at a prochiral center, modest diastereoselectivities were observed with the formation of the new stereogenic carbon. NMR experiments indicate that the addition reaction is reversible under acidic conditions.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01724

DOI: 10.1021/acs.joc.7b01724

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