Direct catalytic asymmetric Mannich-type reaction of thioamides.
Taking the reins: The title transformation of thioamides and N-diphenylphosphinoyl imines is described. By harnessing the power of cooperative catalysis between a soft Lewis acid and a hard Brønsted base, thioamide carbon pronucleophiles can furnish Mannich products (see scheme). Divergent transformation of the thioamide functionality highlights the utility of this methodology.
Suzuki
Yuta
Y
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Yazaki
Ryo
R
Kumagai
Naoya
N
Shibasaki
Masakatsu
M
D002384:Catalysis; D007097:Imines / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry*
D007097:Imines; D008352:Mannich Bases; D013854:Thioamides