Highly enantioselective Michael addition of aromatic ketones to nitroolefins promoted by chiral bifunctional primary amine-thiourea catalysts based on saccharides.
[reaction: see text] A new class of thiourea catalysts have been developed which integrate saccharide and primary amine moieties into one small organic molecule. These simple catalysts are shown to be highly enantioselective for direct Michael addition of aromatic ketones to a range of nitroolefins (up to 98% ee).
Liu
Kun
K
Department of Chemistry, Tianjin University, Tianjin 300072, China.
Cui
Han-Feng
HF
Nie
Jing
J
Dong
Ke-Yan
KY
Li
Xiao-Juan
XJ
Ma
Jun-An
JA
D000098:Acetophenones / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000138:chemical synthesis / Q000737:chemistry*
D000098:Acetophenones; D000475:Alkenes; D000588:Amines; D002241:Carbohydrates; D007659:Ketones; D013890:Thiourea; D009584:Nitrogen; C038699:acetophenone