Recyclable Merrifield resin-supported organocatalysts containing pyrrolidine unit through A3-coupling reaction linkage for asymmetric Michael addition.
Merrifield resin-supported pyrrolidine-based chiral organocatalysts A-D through A(3)-coupling reaction linkage have been developed and found to be highly effective catalysts for the Michael addition reaction of ketones with nitrostyrenes. The reactions generated the corresponding products in good yields (up to 92%), excellent enantioselectivities (up to 98% ee), and high diastereoselectivities (up to 99:1 dr). In addition, the catalysts can be reused at least five times without a significant loss of catalytic activity and stereoselectivity.
Liu
Jie
J
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui, People's Republic of China.
Li
Pinhua
P
Zhang
Yicheng
Y
Ren
Kai
K
Wang
Lei
L
Wang
Guanwu
G
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011137:Polystyrenes / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D012997:Solvents; D013053:Spectrophotometry / Q000379:methods; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*; D014050:Toluene / Q000737:chemistry
D007659:Ketones; C095039:Merrifield resin; D011137:Polystyrenes; D011759:Pyrrolidines; D012997:Solvents; D013343:Styrenes; D014050:Toluene; C032519:pyrrolidine