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In the presence of gold catalysts, γ- or δ-heterosubstituted allenes also provide five- or six-membered heterocycles (by exo-cyclization, a) Zhang, Z, Liu, C, Kinder, R. E, Han, X, Qian, H, Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066
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In the presence of gold catalysts, γ- or δ-heterosubstituted allenes also provide five- or six-membered heterocycles (by exo-cyclization): (a) Zhang, Z.; Liu, C.; Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066.
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43
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34447527727
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No reaction takes place if substrate 1 is treated with small amounts of coned HCl alone.
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No reaction takes place if substrate 1 is treated with small amounts of coned HCl alone.
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44
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33645059154
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Representative Procedure and Spectroscopic Data, Synthesis of cis-2-(tert-Butyldimethylsilyloxy)-3-methyl- 5-phenyl-2,5-dihydrofuran (2) To a solution of 1-(tert- butyldimethylsilyloxy)-3-methyl-5-phenylpenta-3,4-dien-2-ol (1, 80 mg, 0.26 mmol) and 2,2′-bipyridine (2.0 mg, 12.8 μmol) in 3 mL of dry CH 2Cl2 was added AuCl3 (2.0 mg, 6.6 μmol, After stirring for 1 h at r.t, the solvent was evaporated, and the residue was purified by column chromatography (SiO2, EtOAc-cyclohexane, 1:10) furnishing 56 mg (70, of the 2,5-dihydrofuran 2 as a slightly yellow oil (dr > 97:3 according to NMR analysis, 1H NMR (400 MHz, C 6D6, δ, 7.50 (d, 3JJ HH, 7.5 Hz, 2 H, 7.29 (m, 2 H, 7.18 (m, 1 H, 5.79 (m, 1 H, 5.34 (m, 1 H, 4.77 (m, 1 H, 3.86 dd, 2JHH, 10.6 Hz, 3J
-
3): δ = 142.3, 137.4, 128.1, 127.5, 126.9, 125.4, 88.5, 86.7, 65.2, 25.8, 18.3, 12.6, -5.5, -5.6 ppm.
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