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1
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48349085347
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ICREA Researcher at University of Barcelona
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ICREA Researcher at University of Barcelona.
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2
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38349178582
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(b) For an excellent review of asymmetric synthesis enabled by metal-free catalysis, see: Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 3, 79.
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33746507261
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and references cited therein
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Viranyi, A.; Marth, G.; Dancso, A.; Blasko, G.; Toke, L.; Nyerges, M. Tetrahedron 2006, 62, 8720; and references cited therein.
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Chloroform was bought from Aldrich and was used as received
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Chloroform was bought from Aldrich and was used as received.
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48349096366
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Typical Experimental Procedure for the Three-Component Synthesis of Pyrrolidine Derivatives To a stirred solution of aldehyde 3 (0.375 mmol, 1.5 equiv) in CHCl3 (0.5 mL) at r.t, diethyl 2-aminomalonate (2a, 0.375 mmol, 1.5 equiv) was added. The reaction was stirred at r.t. for 30 min and then nitroalkene 1 was added. The reaction was then stirred at r.t. overnight. Next the crude was purified by silica gel column chromatography to afford the pyrrolidine derivative 4. Compound 4d: colorless oil. 1H NMR (400 MHz, CDCl3, δ, 7.48-7.44 (m, 2 H, 7.33-7.28 (m, 7 H, 5.58 (dd, J, 6.8, 8.0 Hz, 1 H, 5.46 (d, J, 8.4 Hz, 1 H, 5.12 (d, J, 7.2 Hz, 1 H, 4.42-4.21 (m, 2 H, 3.91 (q, J, 7.6 Hz, 1 H, 3.46 (q, J, 7.6 Hz, 1 H, 1.29 (t, J, 7.6 Hz, 3 H, 0.78 (t, J, 7.6 Hz, 3 H, 13C NMR 100 MHz, CDCl3, δ, 171.1, 168.4, 135.7, 134.9
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3): δ = 171.1, 168.4, 135.7, 134.9, 132.4, 131.6, 130.9, 128.9, 128.7, 128.6, 128.3, 122.9, 93.5, 75.9, 63.8, 62.2, 62.0, 51.9, 14.0, 13.3.
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