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Stereoselective Synthesis of Pear Ester

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Chemistry of Natural Compounds Aims and scope

A simple two-step synthesis of ethyl-(2E,4Z)-deca-2,4-dienoate based on Fe-catalyzed cross-coupling of ethyl-(2E,4Z)-5-chloropenta-2,4-dienoate, which was obtained via one-pot oxidation and olefination of readily available (2Z)-3-chloroprop-2-en-1-ol by n-pentylmagnesiumbromide, was developed.

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References

  1. D. E. Heinz and W. G. Jennings, J. Food Sci., 31, 69 (1966).

    Article  CAS  Google Scholar 

  2. Y. H. Hui (ed.), Handbook of Fruit and Vegetable Flavors, Wiley, Hoboken, 2010, 1095 pp.

    Google Scholar 

  3. D. M. Light and J. J. Beck, J. Agric. Food Chem., 58, 7838 (2010).

    Article  CAS  PubMed  Google Scholar 

  4. D. M. Light and A. Knight, J. Agric. Food Chem., 53, 4046 (2005).

    Article  CAS  PubMed  Google Scholar 

  5. G. Ohloff and M. Pawlak, Helv. Chem. Acta, 56, 1176 (1973).

    Article  Google Scholar 

  6. M.-J. Devos, L. Hevesi, P. Bayet, and A. Krief, Tetrahedron Lett., 17, 3911 (1976).

    Article  Google Scholar 

  7. H. J. Bestmann and J. Suss, Liebigs Ann. Chem., 363 (1982).

  8. G. Wang, S. Mohan, and E.-I. Negishi, Proc. Natl. Acad. Sci. USA, 108, 11344 (2011).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. B. Byrne, L. M. L. Lawter, and K. J. Wengenroth, J. Org. Chem., 51, 2607 (1986).

    Article  CAS  Google Scholar 

  10. G. V. M. Sharma and D. Rajagopal, Synth. Commun., 20, 633 (1990).

    Article  CAS  Google Scholar 

  11. I. Bauer and H.-J. Knolker, Chem. Rev., 115, 3170 (2015).

    Article  CAS  PubMed  Google Scholar 

  12. R. N. Shakhmaev, A. Sh. Sunagatullina, and V. V. Zorin, Russ. J. Org. Chem., 49, 669 (2013).

    Article  CAS  Google Scholar 

  13. R. N. Shakhmaev, A. Sh. Sunagatullina, N. V. Emyshaeva, and V. V. Zorin, Chem. Nat. Compd., 51, 127 (2015).

    Article  CAS  Google Scholar 

  14. R. N. Shakhmaev, A. Sh. Sunagatullina, and V. V. Zorin, Russ. J. Org. Chem., 51, 95 (2015).

    Article  CAS  Google Scholar 

  15. R. N. Shakhmaev, A. Sh. Sunagatullina, and V. V. Zorin, Chem. Nat. Compd., 53, 128 (2017).

    Article  CAS  Google Scholar 

  16. R. B. Bedford and P. B. Brenner, “The Development of Iron Catalysts for Cross-Coupling Reactions,” in: Topics in Organometallic Chemistry, 50, 19 (2015).

  17. R. N. Shakhmaev, A. Sh. Sunagatullina, and V. V. Zorin, Russ. J. Gen. Chem., 83, 2018 (2013).

    Article  CAS  Google Scholar 

  18. A. U. Takhautdinova, A. U. Ishbaeva, A. Sh. Sunagatullina, R. N. Shakhmaev, and V. V. Zorin, Bashk. Khim. Zh., 17 (3), 39 (2010).

    CAS  Google Scholar 

  19. A. Sh. Sunagatullina, R. N. Shakhmaev, and V. V. Zorin, Russ J. Org. Chem., 49, 730 (2013).

    Article  CAS  Google Scholar 

  20. H. Firouzabadi and E. Ghaderi, Tetrahedron Lett., 19, 839 (1978).

    Article  Google Scholar 

  21. H. Firouzabadi and Z. Mostafavipoor, Bull. Chem. Soc. Jpn., 56, 914 (1983).

    Article  CAS  Google Scholar 

  22. G. Tojo and M. Fernandez, Oxidation of Alcohols to Aldehydes and Ketones, Springer, 2006, 376 pp.

  23. R. N. Shakhmaev, A. U. Ishbaeva, and V. V. Zorin, Russ. J. Org. Chem., 48, 908 (2013).

    Article  Google Scholar 

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Authors and Affiliations

  1. Ufa State Petroleum Technological University, 1 Kosmonavtov St., Ufa, 450062, Russia

    R. N. Shakhmaev, A. Sh. Sunagatullina, D. A. Akimova & V. V. Zorin

Authors
  1. R. N. Shakhmaev
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  2. A. Sh. Sunagatullina
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  3. D. A. Akimova
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  4. V. V. Zorin
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Corresponding author

Correspondence to R. N. Shakhmaev.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2017, pp. 867–869.

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Shakhmaev, R.N., Sunagatullina, A.S., Akimova, D.A. et al. Stereoselective Synthesis of Pear Ester. Chem Nat Compd 53, 1017–1019 (2017). https://doi.org/10.1007/s10600-017-2191-0

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  • DOI: https://doi.org/10.1007/s10600-017-2191-0

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