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Diastereodirected Alkylation of Ketones and 1,3-Diketones with N-[1H-Indol-3-yl(phenyl)methyl]-N-methylamine by the Michael Reaction

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method has been developed for introducing the 1H-indol-3-yl(phenyl)methyl residue into position 2 of ketones and 1,3-diketones. The principle of bringing in controlled diastereoselectivity based on the configuration of intermediates is demonstrated.

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REFERENCES

  1. B. B. Semenov and Yu. I. Smushkevich, Izv. Akad. Nauk, Ser. Khim., 334 (2002).

  2. V. N. Rusinova, Yu. I. Smushkevich, O, V. Telenkova, M. V. Vasin, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 211 (1974).

  3. M. Passerini, Gazz. Chim. Ital., 65, 933 (1935).

    Google Scholar 

  4. T. Moriya, K. Hagio, and N. Yoneda, Chem. Pharm. Bull., 28, 1711 (1980).

    Google Scholar 

  5. B. B. Semenov, Author's Abstract of Dissertation for Candidate of Chemical Sciences, Moscow (2002).

  6. H. Snyder, C. Smith, and J. Stewart, J. Am. Chem. Soc., 66, 200 (1944).

    Article  Google Scholar 

  7. A. Kamal, A. A. Qureshi, and I. Ahmad, Tetrahedron, 19, 681 (1963).

    Article  Google Scholar 

  8. M. Suzuki, T. Miyahara, R. Yoshioka, M. Miyoshii, and K. Matsumoto, Agric. Biol. Chem., 38, 1709 (1974).

    Google Scholar 

  9. B. B. Semenov and V. G. Granik, Khim.-farm. Zh., 38, No.6, 3 (2004).

    Google Scholar 

  10. R. Aitken and S. N. Kilenyi, Asymmetric Synthesis, Chapman & Hall, New York (1992).

    Google Scholar 

  11. V. Prelog and G. Helmchen, Angew. Chem., Int. Ed. Eng., 94, 614 (1982).

    Google Scholar 

  12. D. Seebach and V. Prelog, Angew. Chem., Int. Ed. Eng., 94, 696 (1982).

    Google Scholar 

  13. K. Mislow and J. Siegel, J. Am. Chem. Soc., 106, 3319 (1984).

    Article  Google Scholar 

  14. B. B. Semenov, Yu. I. Smushkevich, G. V. Grintselev-Knyazev, and M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 543 (2001).

  15. Organic Syntheses, Vol. 6 [Russian translation], Izd. Inostr. Lit., Moscow (1956), p. 50.

  16. V. N. Borisova, E. N. Gordeev, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 357 (1976).

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Authors and Affiliations

  1. Moscow D. I. Mendeleev University of Chemical Technology, Moscow, 125190, Russia

    B. B. Semenov & Yu. I. Smushkevich

  2. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Moscow, 117977, Russia

    I. I. Levina & L. N. Kurkovskaya

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow, 117813, Russia

    K. A. Lysenko

  4. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 117913, Russia

    V. V. Kachala

Authors
  1. B. B. Semenov
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  2. Yu. I. Smushkevich
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  3. I. I. Levina
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  4. L. N. Kurkovskaya
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  5. K. A. Lysenko
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  6. V. V. Kachala
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 848–857, June, 2005.

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Semenov, B.B., Smushkevich, Y.I., Levina, I.I. et al. Diastereodirected Alkylation of Ketones and 1,3-Diketones with N-[1H-Indol-3-yl(phenyl)methyl]-N-methylamine by the Michael Reaction. Chem Heterocycl Compd 41, 730–738 (2005). https://doi.org/10.1007/s10593-005-0213-5

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  • DOI: https://doi.org/10.1007/s10593-005-0213-5

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