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Synthesis of β‑Amino Diaryldienones Using the Mannich Reaction

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journal contribution
posted on 13.05.2019 by N. G. R. Dayan Elshan, Matthew B. Rettig, Michael E. Jung
The Mannich reaction has been used for decades to prepare many pharmaceutically important molecules. Here, using a “double-Mannich−β-elimination” synthetic sequence, we report the synthesis and the characterization details of a novel class of β-amino diaryldienones with prominent antiprostate cancer activity. Through these studies, we correct an erroneous structure in the current literature, present a discussion of the stereochemical outcome of a new reaction, and probe the mechanism(s) of byproduct formation through isotopic studies.