Silver(I) triflate-catalyzed direct synthesis of N-PMP protected α-aminopropargylphosphonates from terminal alkynes

Organic Letters

Volumn 9, Issue 1, 2007, Pages 165-167

  Dodda, Rajasekhar ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZENE; MESYLIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALKYNES; AMINATION; BENZENE; CATALYSIS; MESYLATES; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS;

EID: 33846441240     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0627810     Document Type: Article

References (32)

1. For reviews, see: (a) Aminophosphonic and Aminophosphinic Acids; Kuhkar, V. P., Hudson, H. R., Eds.; John Wiley & Sons: Chichester, UK, 2000.
2. (b) Kafarski, P.; Lejczak, B. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 301-312.
3. (c) Berlicki, L.; Kafarski, P. Curr. Org. Chem. 2005, 9, 1829-1850.
4. Strater, N.; Lipscomb, W. N. Biochemistry 1995, 34, 9200-9210.
5. (a) Umezawa, H. Recent Results Cancer Res. 1980, 75, 115-125.
6. (b) Taylor, A.; Daims, M. A.; Lee, J.; Surgenor, T. Curr. Eye Res. 1982, 2, 47-56.
7. (c) Pulido-Cejudo, G.; Conway, B.; Proulx, P.; Brown, R.; Izaguirre, C. A. Antiviral Res. 1997, 36, 167-177.
8. For a review, see: Uziel, J.; Genet, J. P. Russ. J. Org. Chem. 1997, 33, 1521-1542.
9. (a) Samanta, S.; Zhao, C.-G. J. Am. Chem. Soc. 2006, 128, 7442-7443.
10. (b) Dodda, R.; Zhao, C.-G. Org. Lett. 2006, 8, 4911-4914.
11. Schrader, T.; Kober, R.; Steglich, W. Synthesis 1986, 372-375.
12. Reisser, M.; Maas, G. J. Org. Chem. 2004, 69, 4913-4924.
13. For examples, see: (a) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319-4321;
14. (b) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268-269.
15. (c) Wei, C.; Li, C.-J. Green Chem. 2002, 4, 39-41.
16. (d) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638-5639.
17. (e) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584-9585.
18. (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473-4475.
19. (g) Fischer, C.; Carreira, E. M. Org. Lett. 2004, 6, 1497.
20. (h) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107-1110.
21. (i) Benaglia, M.; Negri, D.; Dell'Anna, G. Tetrahedron Lett. 2004, 45, 8705-8708.
22. (j) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472-1483.
23. (k) Wei, C.; Mague, J. T.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5749-5754.
24. (l) Li, Z.; Wei, C.; Chen, L.; Varma, R. S.; Li, C.-J. Tetrahedron Lett. 2004, 45, 2443-2446.
25. (m) Ju, Y.; Li, C.-J.; Varma, R. S. QSAR Comb. Sci. 2004, 23, 891-894.
26. (n) Bisai, A.; Singh, V. K. Org. Lett. 2006, 8, 2405-2408.
27. (o) Huang, B.; Yao, X.; Li, C.-J. Adv. Synth. Catal. 2006, 348, 1528-1532.
28. (a) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42-44.
29. (b) Ji, J.-X.; Wu, J.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11196-11200.
30. Compounds 2 and 5 were prepared by using a modified procedure originally reported by Hamilton and co-workers, see: Hamilton, R.; McKervey, M. A.; Rafferty, M. D.; Walker, B. J. J. Chem. Soc., Chem. Commun. 1994, 37-38.
31. The PMP group may be readily deprotected, see: (a) Marin, S. D. L.; Martens, T.; Mioskowski, C.; Royer, J. J. Org. Chem. 2005, 70, 10592-10595.
32. (b) Reference 9b.