An enantioselective Brønsted acid catalyzed enamine Mannich reaction

A. Louise Tillman, Darren J. Dixon

    Research output: Contribution to journalArticlepeer-review


    An enantioselective Brønsted acid catalyzed Mannich reaction was developed for acetophenone derived enamines and N-Boc imines. An initial catalyst screen using 20 mol% (R,R)-TADDOL, (R)-BINOL, and (S)-H 8-BINOL, at -20°C in toluene, was performed to identify an appropriate Brønsted acid catalytic system for Mannich reaction of aryl methyl ketone with N-Boc aldamines. It was found that the absence of additives led to formation of only 10% of the product, as under the condition the background reaction was slow. The presence of (R,R)-TADDDOL increased the product formation to three times, but low levels of enantioselection were observed. It was also found that the acceleration was more significant in presence of (R)-BINOL. (S)-H2-BINOL was identified as the optimal catalyst to afford versatile β-amino aryl ketones in good yield and enantiomeric excess.
    Original languageEnglish
    Pages (from-to)606-609
    Number of pages3
    JournalOrganic and Biomolecular Chemistry
    Issue number4
    Publication statusPublished - 2007


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