posted on 2020-04-02, 13:42authored bySean H. Wiedemann, Hidetoshi Noda, Shinji Harada, Shigeki Matsunaga, Masakatsu Shibasaki
A new catalytic aldol-type addition of cyclopropanecarboximides to aldehydes via iodide-mediated ring-opening is presented. The reaction
was found to be catalyzed at 0 °C using either a Sc(OTf)3/NaI system or ScI3. Stereoselective formation of α,α-disubstituted enolates occurred
in situ. γ-Lactams bearing α-carbonyl quaternary stereocenters were obtained in 97−57% yield and dr = 90:10−80:20 after ring closure.