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Volumn 3, Issue 1, 2001, Pages 25-28

Derailing the Wacker oxidation: Development of a palladium-catalyzed amidation reaction

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; AMPHIBIAN VENOM; CARBAMIC ACID DERIVATIVE; KETONE; PALLADIUM; PERHYDROHISTRIONICOTOXIN;

EID: 0035843310     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0066882     Document Type: Article
Times cited : (96)

References (30)
  • 1
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    • Seebach, D.; Matthews, J. L. J. Chem. Soc., Chem. Commun. 1997, 2015. Juaristi, E. In Enantioselective Synthesis of β-amino acids; John Wiley & Sons: New York, 1997.
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  • 14
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    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 463-551
    • Hegedus, L.1
  • 20
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    • note
    • 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.
  • 21
    • 0001843634 scopus 로고
    • 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
    • (1989) Chem. Lett. , pp. 2001
    • Hosokawa, T.1    Sinohara, T.2    Ooka, Y.3    Murahashi, S.-I.4
  • 22
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    • note
    • 13C NMR (500 and 62.5 MHz, respectively) spectroscopy and high-resolution mass spectrometry.
  • 23
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    • note
    • 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.
  • 24
    • 0041457720 scopus 로고    scopus 로고
    • note
    • 2.
  • 25
    • 0001659326 scopus 로고
    • Trost. B. M., Fleming, I., Eds.; Pergamon Press: New York
    • Tsuji, J. In Comprehensive Organic Synthesis; Trost. B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, 449.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 449
    • Tsuji, J.1
  • 26
    • 0032503611 scopus 로고    scopus 로고
    • 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.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5579
    • Takaya, Y.1    Ogasawara, M.2    Hayashi, T.3
  • 27
    • 0000300355 scopus 로고
    • 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.
    • (1987) J. Org. Chem. , vol.52 , pp. 1758
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  • 28
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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.
    • (2000) Org. Lett. , vol.2 , pp. 2699
    • Lei, A.1    Lu, X.2
  • 29
    • 0000987232 scopus 로고    scopus 로고
    • 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.
    • (1996) J. Org. Chem. , vol.61 , pp. 2254
    • Wang, Z.1    Lu, X.2


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