Synthesis and applications of a novel polymer-supported EEDQ reagent

Journal of Combinatorial Chemistry

Volumn 9, Issue 5, 2007, Pages 745-747

  Kakarla, Ramesh ^a   Li, Guo ^a   Gerritz, Samuel W ^a  

^a BRISTOL MYERS SQUIBB RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHOXY 1(2H) QUINOLINECARBOXYLIC ACID ETHYL ESTER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; POLYMER; QUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

INDICATORS AND REAGENTS; POLYMERS; QUINOLINES;

EID: 34948828619     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc070020y     Document Type: Article

References (23)

1. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc, Perkin Trans. 2000, 1, 3815-4195.
2. Keck, G. E.; Sanchez, R.; Wager, C. A. Tetrahedron Lett. 2000, 41, 8673-8676.
3. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
4. Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968, 90, 1651-1652.
5. Brown, J.; Williams, R. E. Can. J. Chem. 1971, 49, 3765-3766.
6. Valuer, E.; Bradley, M. Chem. Commun. 2005, 1164-1166.
7. (a) Wang, S. S. J. Am. Chem. Soc. 1973, 95, 1328-1333.
8. (b) Purchased from Novabiochem.
9. (a) Richter, L. S.; Gadek, T. R. Tetrahedron Lett. 1994, 35, 4705-4706.
10. (b) Krchnak, V.; Flegelova, Z.; Weichsel, A. S.; Lebl, M. Tetrahedron Lett. 1995, 36, 6193-6196.
11. Quinoline loading was determined by nitrogen elemental analysis (1.46 mmol/g). Loading was also calculated by cleavage of quinoline from the resin with 50% TFA in DCM for 2 h and then vacuum concentration to provide 85% recovery.
12. -1 in the IR (KBr) spectra.
13. Chiral purity of Z-Pro-D-Phg-OMe (1, 99.9%) was determined by using Chiralpak AD-H column and it's RT (10.41 min) was compared with the three other possible isomers Z-Pro-Phg-OMe (15.16 min), Z-D-Pro-Phg-OMe (7.51 min), and Z-D-Pro-D-Phg-OMe (8.63 min).
14. O'Brien, P.; Warren, S. J. Chem. Soc. 1996, 17, 2129-2138.
15. Rhyoo, H. Y.; Yoon, Y. A.; Park, H. J.; Chung, Y. K. T. Tetrahedron Lett. 2001, 42, 5045-5048.
16. Carboni, C.; Quaedflies, P. J. L. M.; Broxterman, Q. B.; Linda, P.; Gardossi, L. Tetrahedron Lett. 2004, 45, 9649-9652.
17. Venkov, A. P.; Statkova-Abeghe, S. M. Tetrahedron 1996, 52, 1451-1460.
18. Langlois, M.; Curtat, S. Tetrahedron Lett. 1999, 40, 8563-8566.
19. Slobodan, D. P. J. J. Serb. Chem. Soc. 1986, 51, 395-403.
20. Yudao, M. Synthesis 2003, 2886-2889.
21. Md-Wahab, K. Tetrahedron 2005, 61, 11204-11210.
22. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. S. Synlett 2002, 468-470.
23. Al-Hiari, Y. M. J. Het. Chem. 2005, 42, 647-659.