Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins.
Quinidine was found to catalyze the Michael addition of unprotected 3-substituted oxindoles to nitroolefins in excellent yield and moderate to good diastereoselectivity. Bifunctional quinidine derived thiourea catalyst 10 could catalyze this reaction to afford the major diastereomer in up to 85% ee.
Ding
Miao
M
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, PR China.
Zhou
Feng
F
Qian
Zi-Qing
ZQ
Zhou
Jian
J
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D009584:Nitrogen