Citation: Ma Xiaoyan, Hu Xinjun. Recent Advances in Enantioselective Povarov Reaction with Enamides[J]. Chemistry, ;2018, 81(5): 409-413. shu

Recent Advances in Enantioselective Povarov Reaction with Enamides

Ma Xiaoyan ,
Hu Xinjun

School of Chemical Engineering, Sichuan University of Science & Engineering, Zigong 643000

Received Date: 15 December 2017
Accepted Date: 28 January 2018

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The nitrogen-activated C=C double bonds of enamides have considerable potential for use in the construction of various nitrogen-containing products, and organocatalyzed α, β-difunctionalization of nitrogen-activated double bonds proved to be an efficient and versatile concept, and allowed us to obtain a wide range of useful building blocks. The Povarov reaction with enamides, an extended method for vicinal difunctionalization, provides a straightforward and modular entry to 4-amino-1, 2, 3, 4-tetrahydroquinolines. Despite its importance, it was only very recently that several highly efficient catalytic asymmetric protocols for this reaction have been developed as summarized in this review.
- Enamides,
- Difunctionalization,
- Povarov reaction,
- Asymmetric catalysis,
- Tetrahydroquinolines
1. [1]
  D R Carbery. Org. Biomol. Chem., 2008, 6(19):3455~3460.
2. [2]
  G R Dake. Synlett, 2012, 23(6):814~824.
3. [3]
  M X Wang. Chem. Commun., 2015, 51(28):6039~6049.
4. [4]
  T Courant, G Dagousset, G Masson. Synthesis, 2015, 47(13):1799~1856.
5. [5]
  G Bernadat, G Masson. Synlett, 2014, 25(20):2842~2867.
6. [6]
  N Gigant, L Chausset-Boissarie, I Gillaizeau. Chem. Eur. J., 2014, 20(25):7548~7564.
7. [7]
  M Fochi, L Caruana, L Bernardi. Synthesis, 2014, 46(2):135~157.
8. [8]
  V A Glushkov, A G Tolstikov. Russ. Chem. Rev., 2008, 77(2):137~159.
9. [9]
  V V Kouznetsov. Tetrahedron, 2009, 65(14):2721~2750.
10. [10]
  G Masson, C Lalli, M Benohoud et al. Chem. Soc. Rev., 2013, 42(3):902~923.
11. [11]
  P D Leeson, R W Carling, K W Moore et al. J. Med. Chem., 1992, 35(11):1954~1968.
12. [12]
  K M Witherup, R W Ransom, A C Graham et al. J. Am. Chem. Soc., 1995, 117(25):6682~6685.
13. [13]
  Y Xia, Z Y Yang, P Xia et al. J. Med. Chem., 1998, 41(7):1155~1162.
14. [14]
  R Di Fabio, E Tranquillini, B Bertani et al. Bioorg. Med. Chem. Lett., 2003, 13(21):3863~3866.
15. [15]
  M Guinó, P H Phua, J C Caille et al. J. Org. Chem. 2007, 72(16):6290~6293.
16. [16]
  H Liu, G Dagousset, G Masson et al. J. Am. Chem. Soc., 2009, 131(13):4598~4599.
17. [17]
  C Wang, Z Y Han, H W Luo et al. Org. Lett., 2010, 12(10):2266~2269.
18. [18]
  G Dagousset, J Zhu, G Masson et al. J. Am. Chem. Soc., 2011, 133(37):14804~14813.
19. [19]
  G Dagousset, P Retailleau, G Masson et al. Chem. Eur. J., 2012, 18(19):5869~5873.
20. [20]
  J H Lin, G Zong, R B Du et al. Chem. Commun., 2012, 48(62):7738~7740.
21. [21]
  D Huang, F Xu, T Chen et al. RSC Adv., 2013, 3(2):573~578.
22. [22]
  J Brioche, T Courant, L Alcarez et al. Adv. Synth. Catal., 2014, 356(8):1719~1724.
23. [23]
  H Xu, S J Zuend, M G Woll et al. Science, 2010, 327(5968):986~990.
24. [24]
  C Min, N Mittal, D X Sun et al. Angew. Chem. Int. Ed., 2013, 52(52):14084~14088.
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