Mixing of acryloylchloride, dienone 2, N,N-diisopropylethylamine with chiral organocatalyst 5a, which could simultaneously act as Brønsted and Lewis base catalysts, led to a one-pot amidation/Rauhut-Currier sequence, affording α-methylidene-γ-lactams 4. Catalyst 5a could be recovered and reused by acid/base extraction without any loss of catalytic activity in the stepwise protocol.
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Multifunctional catalysis: stereoselective construction of α-methylidene-γ-lactams via an amidation/Rauhut-Currier sequence.
Chem Commun (Camb)
July 2017
The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan.
Mixing of acryloylchloride, dienone 2, N,N-diisopropylethylamine with chiral organocatalyst 5a, which could simultaneously act as Brønsted and Lewis base catalysts, led to a one-pot amidation/Rauhut-Currier sequence, affording α-methylidene-γ-lactams 4. Catalyst 5a could be recovered and reused by acid/base extraction without any loss of catalytic activity in the stepwise protocol.
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