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Discovery of the Double [3+2] Photocycloaddition

  • Jason A. Woolford
Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

As mentioned the Penkett group has performed a wide range of intramolecular palladium induced fragmentation-cyclizations on meta photocycloadducts with the aim of generating molecular complexity in a rapid, simple fashion with sights firmly set toward forming carbon–carbon bonds in natural products.

Keywords

Allyl Alcohol Flash Column Chromatography Cyclopropane Ring Magnesium Bromide Tricyclic Compound 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Penkett CS, Sims RO, French R, Dray L, Roome SJ, Hitchcock PB (2004) Chem Commun 17:1932CrossRefGoogle Scholar
  2. 2.
    Penkett CS, Sims RO, Byrne PW, Kingston L, French R, Dray L, Berritt S, Lai J, Avent AG, Hitchcock PB (2006) Tetrahedron 62:3423CrossRefGoogle Scholar
  3. 3.
    Penkett CS, Sims RO, Byrne PW, Berritt S, Pennicott LE, Rushton SP, Avent AG, Hitchcock PB (2006) Tetrahedron 62:9403CrossRefGoogle Scholar
  4. 4.
    Brann P, Kahan R, Cole S, Penkett CS, Woolford JA (2010) Unpublished workGoogle Scholar
  5. 5.
    Wender PA, Dore TM, de Long MA (1996) Tetrahedron Lett 37:7687CrossRefGoogle Scholar
  6. 6.
    Dewar J (1867) Proc Royal Soc Edinburgh 6:96Google Scholar
  7. 7.
    Horspool W, Armesto D (1992) Organic photochemistry: a comprehensive treatment. Ellis Horwood/PTR Prentice Hall, England/New York, pp 118–125Google Scholar
  8. 8.
    Cornelisse J (1993) Chem Rev 93:615CrossRefGoogle Scholar
  9. 9.
    De Keukeleire D (1994) Aldrichimica Atca 27:59Google Scholar
  10. 10.
    Wender PA, Siggel L, Nuss, JM (1989) Organic photochemistry. Padwa A (ed) vol 10. Marcel Dekker, NewYork, 357–473Google Scholar
  11. 11.
    CDCl3 used for NMR analysis was usually run through a plug of alumina to remove H2O and trace acidGoogle Scholar
  12. 12.
    De Keukeleire D, He S-H (1992) J Chem Soc Chem Comm 5:419CrossRefGoogle Scholar
  13. 13.
    Wender PA, Siggel L, Nuss JM (1991) Comprehensive organic synthesis. Trost BM, Fleming I (eds) vol 5. Pergamon Press, Oxford, 645–673Google Scholar
  14. 14.
    De Keukeleire D, He SL (1993) Chem Rev 93:359CrossRefGoogle Scholar
  15. 15.
    Müller F, Mattay J (1993) Chem Rev 93:99CrossRefGoogle Scholar
  16. 16.
    Wender PA, Dore TM (1995) CRC handbook of organic photochemistry and photobiology. Horspool WM, Song P-S (eds) Ch 22. CRC Press, Boca Raton, 280–290Google Scholar
  17. 17.
    Hoffmann N (2004) Synth 4:481CrossRefGoogle Scholar
  18. 18.
    Chappell D, Russell AT (2006) Org Biomol Chem 4:4409CrossRefGoogle Scholar
  19. 19.
    Mattay J (2007) Angew Chem Int Ed 46:663CrossRefGoogle Scholar
  20. 20.
    Hoffman N (2008) Chem Rev 108:1052CrossRefGoogle Scholar
  21. 21.
    Streit U, Bochet CG (2008) Chimia 62:962CrossRefGoogle Scholar
  22. 22.
    Vizvardi K, Toppet S, Hoornaert GJ, De Keukeleire D, Bako P, Van Der Eycken E (2000) J Photochem Photobiol A Chem 133:135CrossRefGoogle Scholar
  23. 23.
    Van Der Eycken E, De Keukeleire D, De Bruyn A (1995) Tetrahedron Lett 36:3573CrossRefGoogle Scholar
  24. 24.
    Dean EW, Stark DD (1920) A convenient method for the determination of water in petroleum and other organic emulsions. Ind Eng Chem 12:486CrossRefGoogle Scholar
  25. 25.
    Tsunoda T, Suzuki M, Noyori R (1980) Tetrahedron Lett 21:357Google Scholar
  26. 26.
    Kurihara M, Hakamata WJ (2003) Org Chem 68:3413CrossRefGoogle Scholar
  27. 27.
    Clark Still WJ (1976) Org Chem 41:3620CrossRefGoogle Scholar
  28. 28.
    Fickes GN, Metz TE (1978) J Org Chem 43:4057CrossRefGoogle Scholar
  29. 29.
    Nunn EE (1976) Tetrahedron Lett 46:4199CrossRefGoogle Scholar
  30. 30.
    Fenton GA, Gilbert A (1989) Tetrahedron 45:2979CrossRefGoogle Scholar
  31. 31.
    Subrahmanyam G (1976) Indian J Chem B Org Med Chem 14:365Google Scholar
  32. 32.
    Ma B, Snyder JK (2005) Tetrahedron Lett 46:703CrossRefGoogle Scholar
  33. 33.
    Hours AE, Synder JK (2006) Tetrahedron Lett 47:675CrossRefGoogle Scholar
  34. 34.
    Muller F, Mattay J (1993) Chem Rev 93:99CrossRefGoogle Scholar
  35. 35.
    Tomioka H, Kobayashi D, Hashimoto A, Murata S (1989) Tetrahedron Lett 30:4685CrossRefGoogle Scholar
  36. 36.
    Penkett CS, Woolford JA, Day IJ, Coles MP (2010) J Am Chem Soc 123:4CrossRefGoogle Scholar
  37. 37.
    Penkett CS, Woolford JA, Read TW, Kahan RJ (2011) J Org Chem 76:1295CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2011

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of SussexFalmer, BrightonUK

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