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20444492990
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note
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4 (146 mg, 0.689 mmol). After the flask was flushed with nitrogen three times, 1.5 mL of toluene was added, followed by ligand 1 (8.1 μL, 7.4 mg, 52 μmol) and then 1-iodo-3-methylbuta-1,2-diene (70 μL, 114 mg, 0.587 mmol). The flask was covered with aluminum foil and heated to 85°C for 7 h. The reaction was cooled and added to 10 mL of water and then extracted with ethyl acetate (3 x 5 mL), washed with brine, dried over magnesium sulfate, and concentrated under vacuum. The residue was purified by column chromatography on silica gel (eluted with 95% ether, 5% triethylamine) to afford the allenamide (51 mg, 97%) as an oil.
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37
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37049129715
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This allene was prepared by a modification of the procedure of Landor et al.: Greaves, P. M.; Kalli, M.; Landor, P. D.; Landor, S. R. J. Chem. Soc. C 1971, 667.
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40
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20444446115
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note
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To mitigate isomerization to 1,3-dienes, column chromatography on all products was performed with 5% triethylamine in the eluting phase.
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41
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0347928822
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This allene was prepared from the mesylate of 1-hexyn-3-ol following the procedure of Tanaka et al.: Ohno, H.; Ando, K.; Hamaguchi, H.; Takeoka, Y.; Tanaka, T. J. Am. Chem. Soc. 2002, 124, 15255.
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46
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37049117283
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This allene was prepared by a modification of the procedure of Landor, et al.: Landor, S. R.; Patel, A. N.; Whiter, P. F.; Greaves, P. M. J. Chem. Soc. C 1966, 1223.
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