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We recently developed the first synthetically useful enantioselective conjugate addition of cyanide to enones using a polymetallic Gd catalyst. See: Tanaka, Y, Kanai, M, Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 6072
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We recently developed the first synthetically useful enantioselective conjugate addition of cyanide to enones using a polymetallic Gd catalyst. See: Tanaka, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 6072.
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6
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0037448902
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For catalytic enantioselective conjugate addition of cyanide to α,β-unsaturated carboxylic acid derivatives, see: a
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For catalytic enantioselective conjugate addition of cyanide to α,β-unsaturated carboxylic acid derivatives, see: (a) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442.
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(a) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312.
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(b) Yamatsugu, K.; Kamijo, S.; Suto, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 48, 1403.
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2).
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2).
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52949107133
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3 in some cases, leading to diminished yields of the 1,4-products. For example, when 2-cyclohepten-1-one (1c) was used as a substrate, the reaction using TMSCN produced a complex mixture, yielding only 40% of the 1,4-addition product. On the other hand, the reaction using TBSCN was clean, yielding 92% of 3c.
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3 in some cases, leading to diminished yields of the 1,4-products. For example, when 2-cyclohepten-1-one (1c) was used as a substrate, the reaction using TMSCN produced a complex mixture, yielding only 40% of the 1,4-addition product. On the other hand, the reaction using TBSCN was clean, yielding 92% of 3c.
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33847633018
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For previous examples of Ni(0) and Lewis acid catalyzed reactions, see: (a) Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428.
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For previous examples of Ni(0) and Lewis acid catalyzed reactions, see: (a) Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428.
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In the absence of Gd(OTf)3, TBSCN was not an effective nucleophile; the yield of 3b decreased to as low as 6% using TBSCN in the absence of Gd(OTf)3, whereas the yield was 77% using TMSCN in the absence of Gd(OTf)3 Table 3, entry 3
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3 (Table 3, entry 3).
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52949137810
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General Procedure for Ni/Gd(OTf)3-Catalyzed Conjugate Addition of Cyanide to Enones (Table 2, entry 4) The reaction was performed using degassed solvents under Ar atmosphere. To a solution of Ni(cod) 2 (1.7 mg, 0.006 mmol) in THF (0.2 mL, norbornadiene (1.83 μL, 0.018 mmol) was added. Gadolinium triflate (3.6 mg, 0.006 mmol) was added to the mixture, followed by the addition of 2-cyclohexene-1-one (1b: 29.0 μL, 0.30 mmol, Then, TBSCN (63.6 mg, 0.45 mmol) in THF (0.1 mL) was added to start the reaction. After stirring for 1 h, the reaction mixture was directly loaded on SiO2 column (Caution! Highly toxic HCN is generated in this step. This operation should be conducted in a well-ventilated hood, and purified by flash column chromatography (SiO2, Et2O- hexane, 1:20) to afford 3b (62.6 mg, 0.264 mol) in 89% yield
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2O- hexane, 1:20) to afford 3b (62.6 mg, 0.264 mol) in 89% yield.
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