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Volumn 48, Issue 22, 2007, Pages 3867-3870

The CuI-catalyzed exo-selective asymmetric multicomponent [C+NC+CC] coupling reaction

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; PROLINE DERIVATIVE; SILVER;

EID: 34247631632     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.145     Document Type: Article
Times cited : (26)

References (35)
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    • (1993) Advances in Cycloaddition , vol.3 , pp. 161
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    • Kanemasa S., and Tsuge O. In: Curran D.P. (Ed). Advances in Cycloaddition Vol. 3 (1993), JAI Press, Greenwich CT 99
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    • For some recent reviews of asymmetric azomethine ylide cycloaddition, see:
    • For some recent reviews of asymmetric azomethine ylide cycloaddition, see:. Husinec S., and Savic V. Tetrahedron: Asymmetry 16 (2005) 2047
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 2047
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    • Trans-4,5-disubstituted proline derivatives may also be synthesized via formally endo [3+2] cycloadditions of cyclic (E,Z)-azomethine ylides. This approach is illustrated by the work of Williams and Harwood:
    • Trans-4,5-disubstituted proline derivatives may also be synthesized via formally endo [3+2] cycloadditions of cyclic (E,Z)-azomethine ylides. This approach is illustrated by the work of Williams and Harwood:. Williams R.M., Zhai W., Aldous D.J., and Aldous S.C. J. Org. Chem. 57 (1992) 6527
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    • DX-52-1 has been recently shown to inhibit cell migration by virtue of its specific interaction with the ERM protein radixin. See:
    • DX-52-1 has been recently shown to inhibit cell migration by virtue of its specific interaction with the ERM protein radixin. See:. Kahsai A.W., Zhu S., Wardrop D.J., Lane W.S., and Fenteany G. Chem. Biol. 13 (2006) 973
    • (2006) Chem. Biol. , vol.13 , pp. 973
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    • For a comprehesive review of synthetic approaches to DX-52-1 as well as the structurally related tetrahydroisoquinoline antibiotics quinocarcin, tetrazomine, and lemonomycin, see: and references cited therein.
    • For a comprehesive review of synthetic approaches to DX-52-1 as well as the structurally related tetrahydroisoquinoline antibiotics quinocarcin, tetrazomine, and lemonomycin, see:. Scott J.D., and Williams R.M. Chem. Rev. 102 (2002) 166 and references cited therein.
    • (2002) Chem. Rev. , vol.102 , pp. 166
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    • Erratum:
    • Erratum:. J. Am. Chem. Soc. 125 (2003) 4958
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4958
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    • Spirotryprostatin A is an inhibitor of cell cycle progression at the G2/M phase. See:
    • Spirotryprostatin A is an inhibitor of cell cycle progression at the G2/M phase. See:. Cui C.-B., Kakeya H., and Osada H. Tetrahedron 52 (1996) 12651
    • (1996) Tetrahedron , vol.52 , pp. 12651
    • Cui, C.-B.1    Kakeya, H.2    Osada, H.3
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    • note
    • Abbreviations: dppb = 1,4-bis(diphenylphosphino)butane and dppf = 1,1′-bis(diphenylphosphino)ferrocene.
  • 29
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    • note
    • The mixture of cycloadduct 1 and a minor diastereomer (dia-1) was converted to their n-octylthiol esters using the buffered thiolate conditions described previously (Ref. 1). The proton NMR spectrum of the major component (compound 13 in the Supplementary data) did not match the previously prepared endo n-octylthiol ester. The signals for the minor component did match the endo n-octylthiol ester, proving that the mixture of 1/dia-1 consisted of exo and endo isomers and not diastereofacial isomers.
  • 30
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    • note
    • CCDC-642220 (14) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif.
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    • Michael additions of stabilized N-metalated azomethine ylides are known (see Refs. 2a,b). Step-wise [3+2] cycloadditions of stabilized N-metalated azomethine ylides and nitroalkenes have been predicted computationally and demonstrated experimentally. See:
    • Michael additions of stabilized N-metalated azomethine ylides are known (see Refs. 2a,b). Step-wise [3+2] cycloadditions of stabilized N-metalated azomethine ylides and nitroalkenes have been predicted computationally and demonstrated experimentally. See:. Tatsukawa A., Kawatake K., Kanemasa S., and Rudzinski J.M. J. Chem. Soc., Perkin Trans. 2 (1994) 2525
    • (1994) J. Chem. Soc., Perkin Trans. 2 , pp. 2525
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    • Ref. 8.
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    • note
    • Additional support for this interpretation comes from experiments using N-phenylmaleimide, which led to the endo product exclusively. In this case, the EWG and Y groups in structure III are constrained to be cis to each other.


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