Highly enantioselective zinc/BINOL-catalyzed alkynylation of α-ketoimine ester: a new entry to optically active quaternary α-CF3α-amino acids

Chemical Communications

Volumn 47, Issue 19, 2011, Pages 5587-5589

  Huang, Gaochao ^a   Yang, Jie ^b   Zhang, Xingang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b Graduate School of Southwest Petroleum University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALPHA TRIFLUOROMETHYL ALPHA AMINO ACID; AMINO ACID DERIVATIVE; IMINE; KETOIMINE (ALPHA TRIFLUOROMETHYL KETOIMINE ESTER); UNCLASSIFIED DRUG; ZINC;

ALKYNYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; ENANTIOSELECTIVITY; HYDROGENATION; X RAY CRYSTALLOGRAPHY;

EID: 79955166083     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc10403a     Document Type: Article

References (38)

1. A. Giannis, T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244.
2. L. Gentilucci, A. Tolomelli, F. Squassabia, Curr. Med. Chem., 2006, 13, 2449.
3. D. Seebach, J. Gardiner, Acc. Chem. Res., 2008, 41, 1366.
4. R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev., 2008, 37, 1727.
5. X.-L. Qiu, W.-D. Meng, F.-L. Qing, Tetrahedron, 2004, 60, 6711.
6. M. Zanda, New J. Chem., 2004, 28, 1401.
7. V. A. Soloshonok, I. I. Gerus, Y. L. Yagupolskii, Zh. Org. Khim., 1986, 22, 1335.
8. J. T. Welch, A. Gyenes and M. J. Jung, in General Features of Biological Activity of Fluorinated Amino Acids: Design, Pharmacology and Biochemistry, ed. V. P. Kuhhar and V. A. Soloshonok, John Wiley & Sons, Chichester, 1995, pp. 311-331.
9. R. Smits, B. Koksch, Curr. Top. Med. Chem., 2006, 16, 1483.
10. S. Fustero, J. F. Sanz-Cervera, J. L. Acena, M. Sanchez-Rosello, Synlett, 2009, 525.
11. M. Crucianelli, F. D. Angelis, F. Lazzaro, L. Malpezzi, A. Volonterio, M. Zanda, J. Fluorine Chem., 2004, 125, 573.
12. D. Enders, K. Gottfried, G. Raabe, Adv. Synth. Catal., 2010, 352, 3147.
13. P. Fu, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc., 2008, 130, 5530.
14. C. Lauzon, A. B. Charette, Org. Lett., 2006, 8, 2743.
15. Q.-Q. Min, C.-Y. He, H. Zhou, X. Zhang, Chem. Commun., 2010, 46, 8029.
16. J. W. Corbett, S. S. Ko, J. D. Rodgers, L. A. Gearhart, N. A. Magnus, L. T. Bacheler, S. Diamond, S. Jeffrey, R. M. Klabe, B. C. Cordova, S. Garber, K. Logue, G. L. Trainor, P. S. Anderson, S. K. Erickson-Viitanen, J. Med. Chem., 2000, 43, 2019.
17. R. W. King, R. M. Klabe, C. D. Reid, S. K. Erickson-Viitanen, Antimicrob. Agents Chemother., 2002, 46, 1640.
18. B. Jiang, Y.-G. Si, Angew. Chem., Int. Ed., 2004, 43, 216.
19. B. M. Trost, A. H. Weiss, Adv. Synth. Catal., 2009, 351, 963.
20. P. Armas, D. Tejedor, F. Garcia-Tellado, Angew. Chem., Int. Ed., 2010, 49, 1013.
21. L. Zani, C. Bolm, Chem. Commun., 2006, 4263.
22. S. Nakamura, M. Ohara, Y. Nakamura, N. Shibata, T. Toru, Chem.-Eur. J., 2010, 16, 2360.
23. Y. Lu, T. C. Johnstone, B. A. Arndtsen, J. Am. Chem. Soc., 2009, 131, 11284.
24. G. Blay, L. Cardona, E. Climent, J. R. Pedro, Angew. Chem., Int. Ed., 2008, 47, 5593.
25. C. Wei, C.-J. Li, J. Am. Chem. Soc., 2002, 124, 5638.
26. C. Wei, J. T. Mague, C.-J. Li, Proc. Natl. Acad. Sci. U. S. A., 2004, 101, 5749.
27. J.-X. Ji, J. Wu, A. S. C. Chan, Proc. Natl. Acad. Sci. U. S. A., 2005, 102, 11196.
28. M. Shibasaki, M. Kanai, Chem. Rev., 2008, 108, 2853.
29. M. Bella, T. Gasperi, Synthesis, 2009, 1583.
30. O. Riant, J. Hannedouche, Org. Biomol. Chem., 2007, 5, 873.
31. L. Zani, S. Alesi, P. G. Cozzi, C. Bolm, J. Org. Chem., 2006, 71, 1558.
32. L. Zani, T. Eichhorn, C. Bolm, Chem.-Eur. J., 2007, 13, 2587.
33. L. Pu, H.-B. Yu, Chem. Rev., 2001, 101, 757.
34. G. Lu, X. Li, X. Jia, W. L. Chan, A. S. C. Chan, Angew. Chem., Int. Ed., 2003, 42, 5057.
35. Y. Zhou, R. Wang, Z. Xu, W. Yan, L. Liu, Y. Kang, Z. Han, Org. Lett., 2004, 6, 4147.
36. V. A. Soloshonok, Angew. Chem., Int. Ed., 2006, 45, 766.
37. V. A. Soloshonok, D. O. Berbasov, Chim. Oggi/Chem. Today, 2006, 24, 44.
38. V. A. Soloshonok, H. Ueki, M. Yasumoto, S. Mekala, J. S. Hirschi, D. A. Singleton, J. Am. Chem. Soc., 2007, 129, 12112.