New Types of Reactivity of α, β??Unsaturated N, N??Dimethylhydrazones: Chemodivergent Diastereoselective Synthesis of Functionalized Tetrahydroquinolines and …

…, P Ribelles, V Estévez, M Villacampa…

Index: Sridharan, Vellaisamy; Ribelles, Pascual; Estevez, Veronica; Villacampa, Mercedes; Ramos, M. Teresa; Perumal, Paramasivan T.; Menendez, J. Carlos Chemistry - A European Journal, 2012 , vol. 18, # 16 p. 5056 - 5063

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Citation Number: 12

Abstract

Abstract The indium trichloride-catalyzed reaction between aromatic imines and α, β- unsaturated N, N-dimethylhydrazones in acetonitrile afforded 1, 2, 3, 4-tetrahydroquinolines bearing a hydrazone function at C4 through a one-pot diastereoselective domino process that involves the formation of two C [BOND] C bonds and the controlled generation of two stereocenters, one of which is quaternary. This reaction constitutes the first example of an ...