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For Co-catalyzed 1,4-addition/aldol and Michael cyclization, see: (a) Baik, T.-G.; Luiz, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112.
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For Rh-catalyzed 1,4-addition/aldol cyclization, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
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For Rh-catalyzed 1,4-addition/aldol cyclization, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
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18
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3-catalyzed 1,4-addition/Michael cyclization, see: (a) Wang, L. C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
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3-catalyzed 1,4-addition/Michael cyclization, see: (a) Wang, L. C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
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For catalytic 1,4-addition/cycloallylation, see
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For catalytic 1,4-addition/cycloallylation, see: Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758.
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For Rh-catalyzed 1,4-addition/aldol cyclization, see: Cauble, D. F.; Gipson, J. G.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
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50
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33847048566
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Copper-Catalyzed Enantioselective Tandem Conjugate Addition/N-Nitroso-Aldol Reaction: Typical Procedure: Under an Ar atmosphere, a solution of Cu(OTf)2 (3.6 mg, 0.010 mmol) and the monodentate phosphoramidite (0.020 mmol) in toluene (1 mL) was stirred at r.t. for 1 h. The colorless solution was cooled, 20°C) and the ketone (0.50 mmol) and the diethylzinc solution (1.2 equiv) in hexane (1.0 M, 0.6 mL, 0.6 mmol) were added. After 3 h at -20°C, PhNO (80.2 mg, 0.75 mmol, 1.5 equiv) in anhyd toluene (1.5 mL) was added. After stirring the mixture for 18 h, sat. aq NH4Cl (10 mL) was added to the reaction mixture, and then the reaction mixture was extracted with EtOAc (3 x 10 mL, The combined organic phases were washed with brine and dried over Na2SO4. The solvent was then removed under vacuum. After purification by flash chromatography on silica gel PE-EtOAc, 200:1, the addition product 2a was obtained in 86
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2) = 13.95 min, 22.65 min].
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51
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33847072145
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2 = 0.804, final R indices [I > 2σ(I)] R1 = 0.0419, wR2 = 0.0853 (CCDC no. 618359).
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2 = 0.804, final R indices [I > 2σ(I)] R1 = 0.0419, wR2 = 0.0853 (CCDC no. 618359).
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