Citation: Wang Liming, Lin Geng, Zhao Meijun, Liu Dongyao, Jin Ying. Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines[J]. Chinese Journal of Organic Chemistry, ;2018, 38(3): 642-647. doi: 10.6023/cjoc201708028 shu

Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines

Department of Pharmacy, Jilin Medical University, Jilin 132013

Corresponding author: Jin Ying, jinying2288@163.com
Received Date: 15 August 2017
Revised Date: 15 October 2017
Available Online: 17 March 2017
Fund Project: the National Studentsʼ Program for Innovation and Entrepreneurship Training 201713743010the Department of Education of Jilin Province JJKH20170409KJthe National Natural Science Foundation of China 21102055Project supported by the National Natural Science Foundation of China (No. 21102055), the Department of Education of Jilin Province (No. JJKH20170409KJ) and the National Studentsʼ Program for Innovation and Entrepreneurship Training (No. 201713743010)

Figures(2)

Chiral urea derivatives as organocatalysts were applied in the asymmetric aza-Friedel-Crafts reaction of α-naphthol with 14 N-tosyl aldimines. The desired chiral aminoarylnaphthols were obtained in 70%~86% yields with up to 78% enantiomeric excess (ee) under the screened optimal condition. The catalyst type and the substrate scope were broadened in this methodology.
- chiral urea derivatives,
- asymmetric catalysis,
- α-naphthol,
- aza-Friedel-Crafts reaction
1. [1]
  (a) Bandini M., Melloni A., Umani-Ronchi A. Angew. Chem., Int. Ed. 2004, 43, 550.
  (b) Poulsen T. B., Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
  (c) Nicolaou K. C., Reingruber R., Sarlah D., Bräse, S. J. Am. Chem. Soc. 2009, 131, 2086.
  (d) You S. -L., Cai Q., Zeng M. Chem. Soc. Rev. 2009, 38, 2190.
  (e) Ling J., Lam S. K., Lo B., Lam S., Wong W. -T., Sun J., Chen G., Chiu P. Org. Chem. Front. 2016, 4, 457.
  (f) Li J. J., Tan C. H., Mu X. P., Gong J. X., Yang Z. Chin. J. Chem. 2017, 35, 562.
2. [2]
  (a) Uraguchi D., Sorimachi K., Terada M. J. Am. Chem. Soc. 2004, 126, 11804.
  (b) Wang Y. -Q., Song J., Hong R., Li H. M., Deng L. J. Am. Chem. Soc. 2006, 128, 8156.
  (c) Niu L. -F., Xin Y. -C., Wang R. -L., Jiang F., Xu P. -F., Hui X. -P. Synlett 2010, 765.
  (d) Wang S. -G., You S. -L. Angew. Chem., Int. Ed. 2014, 53, 2194.
  (e) Zhou D., Huang Z., Yu X. T., Wang Y. X., Li J., Wang W., Xie H. X. Org. Lett. 2015, 17, 5554.
  (f) Wang Y. C., Jiang L., Li L., Dai J., Xiong D., Shao Z. H. Angew. Chem., Int. Ed. 2016, 55, 15142.
3. [3]
4. [4]
  (a) Trost B. M., Müller, C. J. Am. Chem. Soc. 2008, 130, 2438.
  (b) Sheng Y. -F., Gu Q., Zhang A. -J., You S. -L. J. Org. Chem. 2009, 74, 6899.
  (c)Wang W. T., Liu X. H., Cao W. D., Wang J., Lin L. L., Feng X. M. Chem. -Eur. J. 2010, 16, 1664.
  (d) Arai T., Awata A., Wasai M., Yokoyama N., Masu H. J. Org. Chem. 2011, 76, 5450.
5. [5]
  (a) Enders D., Seppelt M., Beck T. Adv. Synth. Catal. 2010, 352, 1413.
  (b) Bai S., Liao Y. T., Lin L. L., Luo W. W., Liu X. H., Feng X. M. J. Org. Chem. 2014, 79, 10662.
  (c) Montesinos-Magraner M., Vila C., Cantón R., Blay G., Fernández I., Muñoz M. C., Pedro J. R. Angew. Chem., Int. Ed. 2015, 54, 6320.
  (d) Vuković V. D., Richmond E., Wolf E., Moran J. Angew. Chem., Int. Ed. 2017, 56, 3085.
6. [6]
  (a) Kocovsky P., Vyskocil S., Smrcina M. Chem. Rev. 2003, 103, 3213.
  (b) Shirakawa S., Berger R., Leighton J. L. J. Am. Chem. Soc. 2005, 127, 2858.
  (c) Brandes S., Bella M., Kjærsgaard A., Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 1147.
  (d) Liu T. Y., Cui H. L., Chai Q., Long J., Li B. -J., Wu Y., Ding L. -S., Chen Y. -C. Chem. Commun. 2007, 2228.
  (e) Hong L., Wang L., Sun W. S., Wong K., Wang R. J. Org. Chem. 2009, 74, 6881.
  (f) Rueping M., Nachtsheim B. J. Beilstein J. Org. Chem. 2010, 6, 1007.
  (g) Takizawa S., Arteaga F. A., Yoshida Y., Kodera J., Nagata Y., Sasai H. Dalton Trans. 2013, 42, 11787.
  (h) Takizawa S., Hirata S., Murai K., Fujioka H., Sasai H. Org. Biomol. Chem. 2014, 12, 5827.
  (i) Montesinos-Magraner M., Vila C., Cantón R., Blay G., Fernández I., Muñoz M. C., Pedro J. R. Angew. Chem., Int. Ed. 2015, 54, 6320.
7. [7]
  (a) Liu G. X., Zhang S. L., Li H., Zhang T. Z., Wang W. Org. Lett. 2011, 13, 828.
  (b) Chauhan P., Chimni S. S. Eur. J. Org. Chem. 2011, 1636.
8. [8]
  Kumari P., Jakhar A., Khan N. H., Tak R., Kureshy R. I., Abdi S. H. R., Bajaj H. C...Catal. Commun., 2015, 69:138 doi: 10.1016/j.catcom.2015.06.002
9. [9]
  Li Y. W., Wang L. M., Jin Y., Chang S...Chirality, 2017, 29:458 doi: 10.1002/chir.v29.8
10. [10]
  (a) Cheng L., Liu L., Jia H., Wang D., Chen Y. J., Liu L. J. Org. Chem. 2009, 74, 4650.
  (b) Zhang T. Y., He W., Zhao X. Y., Jin Y.Tetrahedron 2013, 69, 7416.
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