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Volumn 36, Issue 11, 2007, Pages 1328-1329

Asymmetrie bis(alkoxycarbonylation) reaction of cyclic olefins catalyzed by palladium in the presence of copper(I) triflate

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EID: 36849093889     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.1328     Document Type: Article
Times cited : (11)

References (23)
  • 2
    • 36849036955 scopus 로고    scopus 로고
    • ed. by M. Beller, Springer. Berlin
    • b) Catalytic Carhonylation Reactions, ed. by M. Beller, Springer. Berlin, 2006.
    • (2006) Catalytic Carhonylation Reactions
  • 8
    • 33744905322 scopus 로고    scopus 로고
    • and references cited therein
    • Y. Yan, X. Zhang. J. Am. Chem. Soc. 2006, 128, 7198, and references cited therein.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 7198
    • Yan, Y.1    Zhang, X.2
  • 15
    • 0025959704 scopus 로고    scopus 로고
    • Related bis(alkoxycarbonylation); Y. Tamaru, M. Hojo, Z. Yoshida, J. Org. Chem. 1991. 56, 1099;
    • Related bis(alkoxycarbonylation); Y. Tamaru, M. Hojo, Z. Yoshida, J. Org. Chem. 1991. 56, 1099;
  • 19
    • 84858493814 scopus 로고    scopus 로고
    • 1-2 5.12 Hz for 2f (cis) with 8.54 Hz for trans isomer.
    • 1-2 5.12 Hz for 2f (cis) with 8.54 Hz for trans isomer.
  • 20
    • 84858494076 scopus 로고    scopus 로고
    • The representative procedure for If (Entry II, Under an Ar atmosphere, CuOTf(C6H6)0.5 (186 mg. 0.74 mmol) was placed in a flask and a MeOH (6 mL) solution of If (235 mg, 1.47 mmol) and a THF (6 mL) solution of 3 (19 mg, 0.059 mmol) was added. To the mixture. PdCl2 (5.32 mg, 0.030 mmol) was added. The Ar atmosphere was replaced with CO/O2 (ca. 1/1, v/v) and the reaction mixture was stirred for 2d at 60°C. A saturated aqueous solution of NaHCO3 was added and the insoluble substance was filtered off. After the filtrate was extracted with ethyl acetate, the extracts were washed with water and brine, dried over Na2SO4, and condensed in vacuo. The residue was purified by column chromatography and further recycle HPLC to give 2f 245 mg. 60, 92% ee
    • 4), and condensed in vacuo. The residue was purified by column chromatography and further recycle HPLC to give 2f (245 mg. 60%. 92% ee).
  • 21
    • 33244484834 scopus 로고    scopus 로고
    • 3-character of benzylic Pd species. A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 1828.
    • 3-character of benzylic Pd species. A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 1828.
  • 23
    • 36849053962 scopus 로고    scopus 로고
    • The combined substrates obtained from experiments of Entries 10 and 11 in Table 1 were used.
    • The combined substrates obtained from experiments of Entries 10 and 11 in Table 1 were used.


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