Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

Chemical Communications

Volumn 49, Issue 39, 2013, Pages 4238-4240

  Jiang, Jun ^a   Ma, Xiaochu ^a   Liu, Shunying ^a   Qian, Yu ^a   Lv, Fengping ^a   Qiu, Lin ^a   Wu, Xiang ^a   Hu, Wenhao ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIAMINOSUCCINIC ACID DERIVATIVE; AZO COMPOUND; BRONSTED ACID; ESTER DERIVATIVE; MANNICH BASE; PHOSPHORAMIDATE AMMONIUM YLIDE; PHOSPHORAMIDIC ACID DERIVATIVE; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 84876531023     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc36972b     Document Type: Article

References (36)

1. A. Viso, R. F. de la Pradilla, M. Tortosa, A. Garcia, A. Flores, Chem. Rev., 2011, 111, 1
2. R. G. Arrayás, J. C. Carretero, Chem. Soc. Rev., 2009, 38, 1940
3. Z. H. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc., 2008, 130, 2170
4. G. A. Cutting, N. E. Stainforth, M. P. John, G. Kociok-Kohn, M. C. Willis, J. Am. Chem. Soc., 2007, 129, 10632
5. K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc., 2001, 123, 5843
6. M. S. Valle, M. F. Saraiva, P. Retailleau, M. V. de Almeida, R. H. Dodd, J. Org. Chem., 2012, 77, 5592
7. W. Q. Zhang, L. F. Cheng, J. Yu, L. Z. Gong, Angew. Chem., Int. Ed., 2012, 51, 4085
8. A. Singh, R. A. Yoder, B. Shen, J. N. Johnston, J. Am. Chem. Soc., 2007, 129, 3466
9. A. Singh, J. N. Johnston, J. Am. Chem. Soc., 2008, 130, 5866
10. T. Davis, J. N. Johnston, Chem. Sci., 2011, 2, 1076
11. Y. N. Belokon, N. I. Chernoglazova, A. S. Batsanov, N. S. Garbalinskaya, V. I. Bakhmutov, Y. T. Struchkov, V. M. Belikov, Russ. Chem. Bull., 1987, 36, 779
12. D. Cież, Tetrahedron, 2007, 63, 4510
13. E. Fernándezmegia, M. M. Paz, F. J. Sardina, J. Org. Chem., 1994, 59, 7643
14. Y. Ozaki, T. Iwasaki, M. Miyoshi, K. Matsumoto, J. Org. Chem., 1979, 44, 1714
15. M. Serizawa, Y. Ukaji, K. Inomata, Tetrahedron: Asymmetry, 2006, 17, 3075
16. K. Zeitler, W. Steglich, J. Org. Chem., 2004, 69, 6134
17. T. Ooi, M. Kameda, J. Fujii, K. Maruoka, Org. Lett., 2004, 6, 2397
18. K. R. Knudsen, K. A. Jørgensen, Org. Biomol. Chem., 2005, 3, 1362
19. A. Puglisi, L. Raimondi, M. Benaglia, M. Bonsignore, S. Rossi, Tetrahedron Lett., 2009, 50, 4340
20. J. Jiang, H.-D. Xu, J.-B. Xi, B.-Y. Ren, F.-P. Lv, X. Guo, L.-Q. Jiang, Z.-Y. Zhang, W.-H. Hu, J. Am. Chem. Soc., 2011, 133, 8428
21. A. Q. Siddiqui, C. Ballatore, C. McGuigan, E. De Clercq, J. Balzarini, J. Med. Chem., 1999, 42, 393
22. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem., Int. Ed., 2004, 43, 1566
23. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal., 2006, 348, 999
24. T. Akiyama, Chem. Rev., 2007, 107, 5744
25. T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc., 2006, 128, 13070
26. T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, Org. Lett., 2005, 7, 2583
27. T. Akiyama, T. Suzuki, K. Mori, Org. Lett., 2009, 11, 2445
28. D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc., 2004, 126, 11804
29. D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc., 2005, 127, 9360
30. M. Terada, K. Sorimachi, J. Am. Chem. Soc., 2007, 129, 292
31. M. Terada, K. Machioka, K. Sorimachi, J. Am. Chem. Soc., 2007, 129, 10336
32. K. Sorimachi, M. Terada, J. Am. Chem. Soc., 2008, 130, 14452
33. H. Qiu, M. Li, L.-Q. Jiang, F.-P. Lv, L. Zan, C.-W. Zhai, M. P. Doyle, W.-H. Hu, Nat. Chem., 2012, 4, 733
34. W.-H. Hu, X.-F. Xu, J. Zhou, W.-J. Liu, H.-X. Huang, J. Hu, L.-P. Yang, L.-Z. Gong, J. Am. Chem. Soc., 2008, 130, 7782
35. X.-F. Xu, J. Zhou, L.-P. Yang, W.-H. Hu, Chem. Commun., 2008, 6564
36. X.-F. Xu, Y. Qian, L.-P. Yang, W.-H. Hu, Chem. Commun., 2011, 47, 797