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note
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No reaction was observed with α,β-unsaturated esters under the conditions described in ref 13. In comparison to the intermediate palladium enolate A/A-I, Scheme 1, the corresponding intermediate developed from the α,β-unsaturated ester we believe would be less stable and hence less likely to form.
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21
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0001843634
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Initial experiments were also conducted using benzyl alcohol. Thus, enone 1b could be converted to the corresponding β-benzyloxy ketone in good yield. This reaction has been noted previously: Hosokawa, T.; Sinohara, T.; Ooka, Y.; Murahashi, S.-I. Chem. Lett. 1989, 2001. However, in our hands their results could not be reproduced and substantial modifications of the reaction conditions were required in order to produce a reliable quantity of the desired product. We also note that 1b was the only enone with which good results could be obtained. equation presented 84 % isolated yield
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Chem. Lett.
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Hosokawa, T.1
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0041457722
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note
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13C NMR (500 and 62.5 MHz, respectively) spectroscopy and high-resolution mass spectrometry.
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23
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0041959081
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note
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Representative procedure: A solution of enone (1 equiv) and benzyl carbamate (1.5 equiv) in anhydrous dichloromethane (1 mL per mmol enone) was added to a stirred solution of bis(acetonitrile)palladium(II) chloride (10 mol %) in anhydrous dichloromethane (1 mL per mmol enone) under an inert atmosphere. The reaction mixture is stirred at room temperature until completion, shown by TLC analysis. The reaction mixture was diluted with diethyl ether and filtered through a pad of silica, and the filtrate was concentrated and purified by flash chromatography.
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24
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0041457720
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note
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2.
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25
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0001659326
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Trost. B. M., Fleming, I., Eds.; Pergamon Press: New York
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Tsuji, J.1
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For examples, see: Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579. Hosokawa, T.; Ohta, T.; Kanayama, S.; Murahashi, S.-I. J. Org. Chem. 1987, 52, 1758. Lei, A.; Lu, X. Org. Lett. 2000, 2, 2699. Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
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For examples, see: Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579. Hosokawa, T.; Ohta, T.; Kanayama, S.; Murahashi, S.-I. J. Org. Chem. 1987, 52, 1758. Lei, A.; Lu, X. Org. Lett. 2000, 2, 2699. Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
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For examples, see: Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579. Hosokawa, T.; Ohta, T.; Kanayama, S.; Murahashi, S.-I. J. Org. Chem. 1987, 52, 1758. Lei, A.; Lu, X. Org. Lett. 2000, 2, 2699. Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
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