Synthesis of novel enantiomerically pure C3-symmetric trialkanolamine ligand containing phosphoryl groups

Synthesis

Volumn , Issue 6, 2006, Pages 989-994

  Wróblewski, Andrzej E ^a   Hałajewska Wosik, Anetta ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

Author keywords

Amino alcohols; Epoxides; Ligands; Phosphonates; Ring opening

Indexed keywords

CATALYSIS; COPPER; ESTERS; MOLECULAR STRUCTURE; STEREOCHEMISTRY;

AMINO ALCOHOLS; EPOXIDES; LIGANDS; PHOSPHONATES; RING OPENING;

SYNTHESIS (CHEMICAL);

ALKANOLAMINE; AMINE; BENZHYDRYLAMINE; BENZYLAMINE; BENZYLOXYAMINE; CALCIUM; CUPROUS ION; DIETHYL 2,3 EPOXYPROPYLPHOSPHONATE; DIPHENHYDRAMINE; IODIDE; LIGAND; METAL; PHOSPHONIC ACID DERIVATIVE; SODIUM CHLORIDE; TRIFLUOROMETHANESULFONIC ACID; TRIS [2(O,O DIETHYLPHOSPHORYLMETHYL)ETHANOL]AMINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENOLYSIS;

EID: 33645370496     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926349     Document Type: Article

References (29)

1. Grassi, M.; Di Silvestro, G.; Farina, M. Tetrahedron 1985, 41, 177.
2. Nugent, W. R.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 6142.
3. Moberg, C. Angew. Chem. Int. Ed. 1998, 37, 248.
4. Di Furia, F.; Licini, G.; Modena, G.; Motterle, R.; Nugent, W. A. J. Org. Chem. 1996, 61, 5175.
5. Bonchio, M.; Licini, G.; Di Furia, F.; Mantovani, S.; Modena, G.; Nugent, W. A. J. Org. Chem. 1999, 64, 1326.
6. Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768.
7. Nugent, W. A. J. Am. Chem. Soc. 1998, 120, 7139.
8. Buonomenna, M. G.; Drioli, E.; Nugent, W. A.; Prins, L. J.; Scrimin, P.; Licini, G. Tetrahedron Lett. 2004, 45, 7515.
9. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
10. Miyano, S.; Lu, L. D.-L.; Viti, S. M.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3608.
11. Michaelson, R. C.; Palermo, R. E.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 1990.
12. Bolm, C.; Bienewald, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2640.
13. Mase, N.; Ohno, T.; Hoshikawa, N.; Ohishi, K.; Morimoto, H.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2003, 44, 4073.
14. Black, C. A.; Ucci, J. W.; Vorpagel, J. S.; Mauck, M. C.; Fenlon, E. E. Bioorg. Med. Chem. Lett. 2002, 12, 3521.
15. Dro, C.; Bellemin-Laponnaz, S.; Welter, R.; Gade, L. H. Angew. Chem. Int. Ed. 2004, 43, 4479.
16. Kim, S.-G.; Kim, K.-H.; Kim, Y. K.; Shin, S. K.; Ahn, K. H. J. Am. Chem. Soc. 2003, 125, 13819.
17. Castaldi, M. P.; Gibson, S. E.; Rudd, M.; White, A. J. P. Angew. Chem. Int. Ed. 2005, 44, 3432.
18. Bringmann, G.; Pfeifer, R.-M.; Rummey, C.; Hartner, K.; Breuning, M. J. Org. Chem. 2003, 68, 6859.
19. Gautier, A.; Mulatier, J.-C.; Crassous, J.; Dutasta, J.-P. Org. Lett. 2005, 7, 1207.
20. Kiss, T.; Lazar, I. In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R., Eds.; Wiley: New York, 2000, 285-326.
21. Wróblewski, A. E.; Hałajewska-Wosik, A. Eur. J. Org. Chem. 2002, 2758.
22. Wróblewski, A. E.; Hałajewska-Wosik, A. Tetrahedron: Asymmetry 2003, 14, 3359.
23. Wróblewski, A. E.; Hałajewska-Wosik, A. Tetrahedron: Asymmetry 2004, 15, 3201.
24. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
25. Favretto, L.; Nugent, W. A.; Licini, G. Tetrahedron Lett. 2002, 43, 2581.
26. Righi, G.; Pescatore, G.; Bonadies, F.; Bonini, C. Tetrahedron 2001, 57, 5649.
27. Zhao, P.-Q.; Xu, L.-W.; Xia, C.-G. Synlett 2004, 846.
28. Chakraborti, A. K.; Rudrawar, S.; Kondaskar, A. Eur. J. Org. Chem. 2004, 3597.
29. Cepanec, I.; Litvi, M.; Mikuldaš, H.; Bartolinčić, A.; Vinković, V. Tetrahedron 2003, 59, 2435.