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http://dx.doi.org/10.5012/bkcs.2014.35.12.3433

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)
Publication Information
Bulletin of the Korean Chemical Society / v.35, no.12, 2014 , pp. 3433-3436 More about this Journal
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
4-Piperidone; N-Unsubstituted imine; Benzyl azide; Synthetic method;
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1 (n) Shintani, R.; Tokunaga, N.; Doi , H.; Hayahsi, T. J. Am. Chem. Soc. 2004, 126, 6240.   DOI   ScienceOn
2 Feng, L.; Xu, L.; Lam, K.; Zhou, Z.; Yip, C. W.; Chan, A. S. C. Tetrahedron Lett. 2005, 46, 8685.   DOI   ScienceOn
3 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.   DOI   ScienceOn
4 Lee, J. H.; Gupta, S.; Jeong, W.; Rhee, Y. H.; Park, J. Angew. Chem. Int. Ed. 2012, 51, 10851.   DOI   ScienceOn
5 (a) Chen, G-M.; Brown, H. C. J. Am. Chem. Soc. 2000, 122, 4217.   DOI   ScienceOn
6 (b) Itsuno, S.; Watanabe, K.; Matsumoto, T.; Kuroda, S.; Yokoi, A.; El-Shehawy, A. J. Chem. Soc., Perkin Trans. 1 1999, 2011.
7 (a) Enders, D.; Grondal, C.; Vrettou, M.; Synthesis 2006, 2155.
8 (b) Lu, M.; Zhu, D.; Lu, Y.; Hou, Y.; Tan, B.; Zhong, G.; Angew. Chem. Int. Ed. 2008, 47, 10187.   DOI   ScienceOn
9 (c) Zhu, D.; Lu, M.; Chua, P. J.; Tan, B.; Wang, F.; Yang, X.; Zhong, G.; Org. Lett. 2008, 10, 4585.   DOI   ScienceOn
10 (d) Tan, B.; Zeng, X.; Lu, Y.; Chua, P. J.; Zhong, G. Org. Lett. 2009, 11, 1927.   DOI   ScienceOn
11 Schmid, M. B.; Zeitler, K.; Gschwind, R. M. Angew. Chem. Int. Ed. 2010, 49, 4997.   DOI   ScienceOn
12 (b) Han, J.; Jeon, M.; Pak,H.; Rhee, Y. H.; Park, J. Adv. Synth. Catal.; DOI 10.1002/adsc.adsc.201400584.
13 (e) Muller, D.; Alexakis, A. Org. Lett. 2012, 14, 1842.   DOI   ScienceOn
14 (d) Guo, F.; Dhakal, R. C.; Dieter, R. K. J. Org. Chem. 2013, 78, 8451.   DOI   ScienceOn
15 (a) Ranade, A. R.; Georg, G. I. J. Org. Chem. 2014, 79, 984.   DOI   ScienceOn
16 (b) Kim, Y. W.; Georg, G. I. Org. Lett. 2014, 16, 1574.   DOI   ScienceOn
17 (f) Zhang, X.; Chen, J.; Han, F.; Cun, L.; Liao, J. Eur. J. Org. Chem. 2011, 1443.
18 (g) Dieter, R. K.; Guo, F. J. Org. Chem. 2009, 74, 3843.   DOI   ScienceOn
19 (h) Clarke, P. A.; Zaytsev, A. V.; Morgan, T. W.; Whitwood, A. C.; Wilson, C. Org. Lett. 2008, 10, 2877.   DOI   ScienceOn
20 (i) Aznar, F.; Garcia, A.; Quinones, N.; Cabal, M. Synthesis 2008, 479.
21 (j) Rosiak, A.; Hoenke, C.; Christoffers, J. Eur. J. Org. Chem. 2007, 4376.
22 (k) Aznar, F.; Garcia, A.; Cabal, M. Adv. Synth. Cata. 2006, 348, 2443.   DOI   ScienceOn
23 (l) Focken, T.; Charette, A. B. Org. Lett. 2006, 8, 2985.   DOI   ScienceOn
24 (c) Vu, H.-D.; Renault, J.; Toupet, L.; Uriac, P.; Gouault, N. Eur. J. Org. Chem. 2013, 6677.
25 (m) R. B. C. Jagt, J. G. deVries, B. L. Feringa, A. J. Minnaard, Org. Lett. 2005, 7, 2433.   DOI   ScienceOn
26 (a) Jeong, W.; Lee, J. H.; Lim, J.; Lee, W. J.; Seong, J.-H.; Park, J.; Rhee, Y. H. RSC Adv. 2014, 4, 20632.   DOI   ScienceOn