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Synthesis of Piperidones from Benzyl Azides and Acetone

  • Han, Junghoon (Department of Chemistry, Pohang University of Science and Technology) ;
  • Rhee, Young Ho (Department of Chemistry, Pohang University of Science and Technology) ;
  • Park, Jaiwook (Department of Chemistry, Pohang University of Science and Technology)
  • Received : 2014.07.21
  • Accepted : 2014.08.04
  • Published : 2014.12.20

Abstract

A new method for the synthesis of 2,2-dimethyl-6-substituted 4-piperidone was developed; two equivalents of acetone were annulated with N-unsubstituted imines in-situ generated from benzyl azides using a ruthenium catalyst in the presence of $\small{L}$-proline.

Keywords

References

  1. (a) Ranade, A. R.; Georg, G. I. J. Org. Chem. 2014, 79, 984. https://doi.org/10.1021/jo402445r
  2. (b) Kim, Y. W.; Georg, G. I. Org. Lett. 2014, 16, 1574. https://doi.org/10.1021/ol500105d
  3. (c) Vu, H.-D.; Renault, J.; Toupet, L.; Uriac, P.; Gouault, N. Eur. J. Org. Chem. 2013, 6677.
  4. (d) Guo, F.; Dhakal, R. C.; Dieter, R. K. J. Org. Chem. 2013, 78, 8451. https://doi.org/10.1021/jo400936z
  5. (e) Muller, D.; Alexakis, A. Org. Lett. 2012, 14, 1842. https://doi.org/10.1021/ol3004436
  6. (f) Zhang, X.; Chen, J.; Han, F.; Cun, L.; Liao, J. Eur. J. Org. Chem. 2011, 1443.
  7. (g) Dieter, R. K.; Guo, F. J. Org. Chem. 2009, 74, 3843. https://doi.org/10.1021/jo900327q
  8. (h) Clarke, P. A.; Zaytsev, A. V.; Morgan, T. W.; Whitwood, A. C.; Wilson, C. Org. Lett. 2008, 10, 2877. https://doi.org/10.1021/ol801051g
  9. (i) Aznar, F.; Garcia, A.; Quinones, N.; Cabal, M. Synthesis 2008, 479.
  10. (j) Rosiak, A.; Hoenke, C.; Christoffers, J. Eur. J. Org. Chem. 2007, 4376.
  11. (k) Aznar, F.; Garcia, A.; Cabal, M. Adv. Synth. Cata. 2006, 348, 2443. https://doi.org/10.1002/adsc.200600318
  12. (l) Focken, T.; Charette, A. B. Org. Lett. 2006, 8, 2985. https://doi.org/10.1021/ol0609006
  13. (m) R. B. C. Jagt, J. G. deVries, B. L. Feringa, A. J. Minnaard, Org. Lett. 2005, 7, 2433. https://doi.org/10.1021/ol050734m
  14. (n) Shintani, R.; Tokunaga, N.; Doi , H.; Hayahsi, T. J. Am. Chem. Soc. 2004, 126, 6240. https://doi.org/10.1021/ja048825m
  15. Feng, L.; Xu, L.; Lam, K.; Zhou, Z.; Yip, C. W.; Chan, A. S. C. Tetrahedron Lett. 2005, 46, 8685. https://doi.org/10.1016/j.tetlet.2005.10.050
  16. Feng, L.-C.; Sun, Y.-W.; Tang, W.-J.; Xu, L.-J.; Lam, K.-L.; Zhou, Z.; Chan, A. S. C. Green Chem. 2010, 12, 949. https://doi.org/10.1039/b926498a
  17. Lee, J. H.; Gupta, S.; Jeong, W.; Rhee, Y. H.; Park, J. Angew. Chem. Int. Ed. 2012, 51, 10851. https://doi.org/10.1002/anie.201204483
  18. (a) Chen, G-M.; Brown, H. C. J. Am. Chem. Soc. 2000, 122, 4217. https://doi.org/10.1021/ja993965v
  19. (b) Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
  20. (a) Jeong, W.; Lee, J. H.; Lim, J.; Lee, W. J.; Seong, J.-H.; Park, J.; Rhee, Y. H. RSC Adv. 2014, 4, 20632. https://doi.org/10.1039/c4ra02941k
  21. (b) Han, J.; Jeon, M.; Pak,H.; Rhee, Y. H.; Park, J. Adv. Synth. Catal.; DOI 10.1002/adsc.adsc.201400584.
  22. (a) Enders, D.; Grondal, C.; Vrettou, M.; Synthesis 2006, 2155.
  23. (b) Lu, M.; Zhu, D.; Lu, Y.; Hou, Y.; Tan, B.; Zhong, G.; Angew. Chem. Int. Ed. 2008, 47, 10187. https://doi.org/10.1002/anie.200803731
  24. (c) Zhu, D.; Lu, M.; Chua, P. J.; Tan, B.; Wang, F.; Yang, X.; Zhong, G.; Org. Lett. 2008, 10, 4585. https://doi.org/10.1021/ol801864c
  25. (d) Tan, B.; Zeng, X.; Lu, Y.; Chua, P. J.; Zhong, G. Org. Lett. 2009, 11, 1927. https://doi.org/10.1021/ol900330p
  26. Schmid, M. B.; Zeitler, K.; Gschwind, R. M. Angew. Chem. Int. Ed. 2010, 49, 4997. https://doi.org/10.1002/anie.200906629

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