Citation: Huang Ling, Zhu Zheng, Cao Tianhua, Lei Xueying, Gong Jiuhan, Guo Shengmei, Cai Hu. Rapid, Practical and Efficient Synthesis of Enol Phosphates from β-Keto Esters and Phosphites[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1571-1576. doi: 10.6023/cjoc201611018 shu

Rapid, Practical and Efficient Synthesis of Enol Phosphates from β-Keto Esters and Phosphites

College of Chemistry, Nanchang University, Nanchang 330031

Corresponding author: Guo Shengmei, Cai Hu, caihu@ncu.edu.cn
Received Date: 16 November 2016
Revised Date: 12 January 2017

Fund Project: the National Natural Science Foundation of China 21302084the National Key Basic Research Program of China 973 Programthe National Key Basic Research Program of China 2012CBA01204

Figures(1)

A useful strategy for the synthesis of enol phosphates from β-keto esters via Atherton-Atodd reaction was developed. A variety of enol phosphates can be quickly and readily prepared with broad substrate scope and moderate yields under mild conditions. This method provides a low cost and practical way to synthesize enol phosphates from β-keto esters.
- enol phosphate,
- β-keto ester,
- Atherton-Todd reaction
1. [1]
  (a) Lindhard, A. T.; Gøgsig, T. M.; Skrystrup, T. J. Org. Chem. 2009, 74, 135.
  (b) Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 12, 1001.
  (c) Lu, Q.; Chen, J.; Liu, C.; Huang, Z. Peng, P. Wang, H.; Lei, A. RSC Adv. 2015, 5, 24494.
  (d) Wang, H.; Lu, Q.; Qian, C.; Liu, C.; Liu, W.; Chen, K.; Lei, A. Angew. Chem., Int. Ed. 2016, 55, 1094.
  (e) Hansen, A. L.; Ebran, J. P.; Gøgsig, T. M.; Skrystrup, T. Chem. Commun. 2006, 4137.
  (f) Gauthier, D.; Beckendorf, S.; Lindhard, A. T.; Gøgsig, T. M.; Skrystrup, T. J. Org. Chem. 2009, 74, 3536.
  (g) Cahiez, G.; Gager, O. Synthesis 2008, 16, 2636.
  (h) Hansen, A. L.; Ebran, J. P.; Gøgsig, T. M.; Skrystrup, T. J. Org. Chem. 2007, 72, 6464.
  (i) Sato, M.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1609.
2. [2]
  (a) Cheruku, P.; Diesen, J.; Andersson, P. G. J. Am. Chem. Soc. 2008, 130, 5595.
  (b) Zhang, W.; Zhang, X. J. Org. Chem. 2007, 72, 1020.
  (c) Tang, W.; Liu, D.; Zhang, X. Org. Lett. 2003, 5, 205.
  (d) Panella, L.; Feringa, B. L.; de Vries, J. G.; Minnaard, A. J. Org. Lett. 2005, 7, 4177.
  (e) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701.
  (f) Cheruku, P.; Gohil, S.; Andersson, P. G. Org. Lett. 2007, 9, 1659.
  (g) Meng, X.; Li, Y.; Xu, D. Tetrahedron: Asymmetry 2009, 20, 1402.
  (h) Biosca, M.; Paptchikhine, A.; Pàmies, O.; Andersson, P. G.; Diéguez, M. Chem. Eur. J. 2015, 21, 3455.
3. [3]
  (a) Boger, D. L. In Modern Organic Synthesis, TSRL Press, La Jolla, CA, 1999, pp. 147~206.
  (b) Mekelburger, H. B.; Wilcox, C. S. Comprehensive Organic Synthesis, Vol. 2, Pergamon, Oxford, 1991, pp. 99~131.
  (c) Carruthers, W.; Coldham, I. Modern Methods of Organic Synthesis, Cambridge University Press, Cambridge, 2004, pp. 9~19.
  (d) Moinizadeh, N.; Klemme, R.; Kansy, M.; Zimmer, R. Reissig, H.-U. Synthesis 2013, 45, 2752.
  (e) Scarpi, D.; Bartali, L.; Casini, A.; Occhiato, E. G. Eur. J. Org. Chem. 2013, 1306.
  (f) Sernissi, L.; Petrovic, M.; Scarpi, D.; Guarna, A.; Trabocchi, A.; Bianchini, F.; Occhiato, E. G. Chem. Eur. J. 2014, 20, 1118.
4. [4]
  (a) Kerr, W. J.; Lindsay, D. M.; Patel, V. K.; Rajamanickama, M. Org. Biomol. Chem. 2015, 13, 10131.
  (b) Ding, Y.; Wang, W.; Liu, Z. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 118, 113.
  (c) Lee, P. H.; Kim, S.; Park, A.; Chary, B. C.; Kim, S. Angew. Chem., Int. Ed. 2010, 49, 6806.
  (d) Song, R.-J.; Liu, Y.-Y.; Wu, J.-C.; Xie, Y.-X.; Deng, G.-B.; Yang, X.-H.; Liu, Y.; Li, J.-H. Synthesis 2012, 44, 1119.
  (e) Zhu, X.-Y.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Tetrahedron 2012, 68, 6032.
  (f) Chary, B. C.; Kim, S.; Shin, D.; Lee, P. H. Chem. Commun. 2011, 47, 7851.
  (g) Barrientos Astigarraga, R. E.; Castelani, P.; Sumida, C. Y.; Zukerman Schpector, J.; Comasseto, J. V. Tetrahedron 2002, 58, 1051.
5. [5]
  (a) Kim, J.; De. Castro, A. K.; Lim, M.; Rhee, H.; Tetrahedron 2010, 66, 3995.
  (b) Sun, P.; Wu, Y.; Yang, T.; Wu, X.; Xu, J.; Lin, A.; Yao, H. Adv. Synth. Catal. 2015, 357, 2469.
  (c) Wang, Z.; Yin, G.; Chen. A.; Hu, S.; Wu, A. Synth. Commun. 2007, 37, 4399.
  (d) Supurgibekov, M. B.; Surya Prakash, G. K.; Nikolaev, V. A. Synthesis 2013, 45, 1215.
  (e) Zhao, Y.; Zhao, J.; Zhou, Y.; Lei, Z.; Li, L.; Zhang, H. New J. Chem. 2005, 29, 769.
  (f) Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176.
  (g) Liu, W.; Liu, J. D.; Nishihara, O. Y.; Guo, X.; Li, Z. Org. Lett. 2011, 13, 6272.
  (h) Ariger, M. A.; Carreira, E. M. Org. Lett. 2012, 14, 4522.
  (i) Koukabi, N.; Kolvari, E.; Zolfigol, M. A.; Khazaei, A.; Shaghasemi, B. S.; Fasahati, B. Adv. Synth. Catal. 2012, 354, 2001.
6. [6]
  (a) Guo, S.; Lu, L.; Gong, J.; Zhu, Z.; Xu, F.; Wei, Z.; Cai, H. Org. Biomol. Chem. 2015, 13, 4426.
  (b) Guo, S.; Zhu, Z.; Lu, Lin, Zhang, W.; Gong, J.; Cai, H. Synlett 2015, 26, 543.
  (c) Guo, S.; Gong, J.; Lu, L.; Zhu, Z.; Cai, H. Chin. J. Org. Chem. 2015, 35, 1348.
  (d) Gong, J.; Zhu, Z.; Lu, L.; Guo, S.; Cai, H. Chin. J. Org. Chem. 2015, 35, 1917.
  (e) Lu, L.; Guo, S.; Xiong, Q.; Liu, S.; Li, X.; Cai, H. Synthesis 2014, 46, 2445.
7. [7]
  (a) Atherton, F. R.; Todd, A. R. J. Chem. Soc. 1947, 674.
  (b) Atherton, F. R.; Openshaw, H, T.; Todd, A. R. J. Chem. Soc. 1945, 660.
  (c) Georgiev, E. M.; Kaneti, J.; Troev, K.; Roundhill, D. M. J. Am. Chem. Soc. 1993, 115, 10964.
  (d) Le Corre, S. S; Berchel, M.; Couthon-Gourvès H.; Haelters, J.-P.; Haffrès, P.-A. Beilstein J. Org. Chem. 2014, 10, 1166.
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