Multiple regioselective functionalizations of quinolines via magnesiations

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5525-5528

  Boudet, Nadège ^a   Lachs, Jennifer R ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MAGNESIUM; QUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM;

MAGNESIUM; QUINOLINES; STEREOISOMERISM;

EID: 38349131107     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702494k     Document Type: Article

References (36)

1. Wiesner, J.; Ortmann, R.; Jomaa, H.; Schlitzer, M. Angew. Chem., Int. Ed. 2003, 42, 5274.
2. Elliott, J. M.; Carling, R. W.; Chambers, M.; Chicchi, G. G.; Hutson, P. H.; Jones, A. B.; MacLeod, A.; Marwood, R.; Meneses-Lorente, G.; Mezzogori, E.; Murray, F.; Rigby, M.; Royo, I.; Russell, M. G. N.; Sohal, B.; Tsao, K. L.; Williams, B. Bioorg. Med. Chem. Lett. 2006, 16, 5748.
3. Duffour, J.; Gourgou, S.; Desseigne, F.; Debrigode, C.; Mineur, L.; Pinguet, F.; Poujol, S.; Chalbos, P.; Bressole, F.; Ychou, M. Cancer Chemother. Pharmacol. 2007, 60, 283.
4. (a) Comins, D. L.; Nolan, J. M. I.; Bori, D. Tetrahedron Lett. 2005, 46, 6697.
5. (b) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059.
6. (c) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120.
7. (d) Arzel, E.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1999, 55, 12149.
8. (e) Marull, M.; Schlosser, M. Eur. J. Org. Chem. 2003, 1569.
9. (f) Marull, M.; Schlosser, M. Eur. J. Org. Chem. 2004, 1008.
10. (g) For review, see: Schlosser, M. Angew. Chem., Int. Ed. 2005, 44, 376.
11. Dumouchel, S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron Lett. 2003, 44, 2033.
12. Kitagawa, K.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2000, 39, 2481.
13. (a) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
14. (b) Boudet, N.; Knochel, P. Org. Lett. 2006, 8, 3737.
15. Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 2958.
16. (a) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
17. (b) The reagent 4 was directly used from commercial sources such as Chemetall GmbH.
18. Clososki, G. C.; Rohbogner, C. J. Angew. Chem., Int. Ed. 2007, 46, 7681.
19. 4Cl (aqueous).
20. 4Cl (aqueous).
21. Osborne, A. G.; Buley, J. M.; Clarke, H.; Dakin, R. C. H.; Price, P. I. J. Chem. Soc., Perkin Trans. 1 1993, 22, 2747.
22. Steck, E. A.; Hallock, L. L.; Holland, A. J. J. Am. Chem. Soc. 1946, 68, 1241.
23. Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349.
24. Mallet, M.; Quéguiner, G. Tetrahedron 1986, 42, 2253.
25. (a) Without the addition of TMEDA, the C3/C4 regioselectivity was found to be 19:1, whereas using TMEDA (1.1 equiv), it was 99:1.
26. (b) For the use of TMEDA, see also: Wang, X. J.; Xu, Y.; Zhang, L.; Krishnamurthy, D.; Senanayake, D. H. Org. Lett. 2006, 8, 3141.
27. Fujiki, K.; Tanifuji, N.; Sasaki, Y.; Yokoyama, T. Synthesis 2002, 343.
28. del Amo, V.; Dubbaka, S. R.; Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 7838.
29. Stoll, A. H.; Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 606.
30. Villieras, J.; Rambaud, M. Org. Synth. 1988, 66, 220.
31. TMPMgCl·LiCl (7) was found to be ineffective for this metalation.
32. Ethyl pinacol borate was preferentially used instead of commercially available isopropyl pinacol borate because of a transesterification side reaction.
33. Brown, H. C.; Bhat, N. G.; Srebnik, M. Tetrahedron Lett. 1988, 29, 2631.
34. Labaw, C. S.; Liu, P. PCT Int. Appl. WO 2007016609, 2007.
35. Kaila, N.; Janz, K.; Huang, A.; Moretto, A.; DeBernardo, S.; Bedard, P. W.; Tam, S.; Clerin, V.; Keith, J. C., Jr.; Tsao, D. H. H.; Sushkova, N.; Shaw, G. D.; Camphausen, R. T.; Schaub, R. G.; Wang, Q. J. Med. Chem. 2007, 50, 21.
36. 4) and concentrated in vacuo. Purification by flash chromatography (n-pentane/diethyl ether = 7:3) yielded 837 mg (84% yield) of 11a as a colorless solid (mp 176.6-177.4°C).