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Synthesis of β‑Amino Diaryldienones Using the Mannich Reaction

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journal contribution
posted on 13.05.2019, 00:00 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.