Selective and multiple functionalization of pyridines and alkaloids via Mg- and Zn-organometallic intermediates

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2306-2309

  Jaric, Milica ^a   Haag, Benjamin A ^a   Manolikakes, Sophia M ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MAGNESIUM; ORGANOMETALLIC COMPOUND; PYRIDINE DERIVATIVE; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

ALKALOIDS; MAGNESIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PYRIDINES; ZINC;

EID: 79955604204     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200563j     Document Type: Article

References (51)

1. Henry, G. D. Tetrahedron 2004, 29, 6043
2. Marazano, C. In Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom; Black, D. S. C., Ed.; Science of Synthesis; Georg Thieme: Stuttgart, 2005; Vol. 1.
3. Schlosser, M.; Mongin, F. Chem. Soc. Rev. 2007, 36, 1161
4. Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K.; Zhdankin, V. V., Eds. Comprehensive Heterocyclic Chemistry III; Elsevier: Oxford, 2008; Vols. 7-9.
5. Hill, M. D. Chem.-Eur. J. 2010, 16, 12052
6. Comins, D. L.; LaMunyon, D. H. Tetrahedron Lett. 1988, 29, 773
7. Snieckus, V. Chem. Rev. 1990, 90, 879
8. Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059
9. Turck, A.; Plé, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489
10. Karig, G.; Spencer, J. A.; Gallagher, T. Org. Lett. 2001, 3, 835
11. Schlosser, M. Angew. Chem., Int. Ed. 2005, 44, 376
12. Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802
13. Gros, P. C.; Fort, Y. Eur. J. Org. Chem. 2009, 4199
14. Khartabil, H. K.; Gros, P. C.; Fort, Y.; Ruiz-López, M. F. J. Am. Chem. Soc. 2010, 132, 2410
15. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
16. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
17. Li, B.; Wu, Z.-H.; Gu, Y.-F.; Sun, C.-L.; Wang, B.-Q.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 1109
18. Prokopcová, H.; Bergman, S. D.; Aelvoet, K.; Smout, V.; Herrebout, W.; Van der Veken, B.; Meerpoel, L.; Maes, B. U. W. Chem.-Eur. J. 2010, 16, 13063
19. Minisci, F.; Fontana, F.; Vismara, E. J. Heterocycl. Chem. 1990, 27, 79
20. Harrowven, D. C.; Sutton, B. J. Prog. Heterocycl. Chem. 2004, 16, 27
21. Seiple, I. B.; Su, S.; Rodriguez, R. A.; Gianatassio, R.; Fujiwara, Y.; Sobel, A. L.; Baran, P. S. J. Am. Chem. Soc. 2010, 132, 13194
22. Joule, J. A.; Mills, K. Heterocyclic Chemistry; Wiley-Blackwell: Chichester, 2010; Vol. 5.
23. Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 2958
24. Jaric, M.; Haag, B. A.; Unsinn, A.; Karaghiosoff, K.; Knochel, P. Angew. Chem., Int. Ed. 2010, 49, 5451
25. Verpoorte, R.; Schripsema, J.; van der Leer, T. Alkaloids 1988, 34, 331
26. Gros, P. C.; Doudouh, A.; Woltermann, C. Org. Biomol. Chem. 2006, 4, 4331
27. Cordell, G. A. The Alkaloids: Chemistry and Biology; Academic Press: Oxford, 2010; Vol. 69.
28. Kessar, S. V.; Singh, P.; Singh, A. K.; Kaul, V. K. Indian J. Chem. 1994, 33B, 818
29. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327
30. Kessar, S. V.; Singh, P. Chem. Rev. 1997, 97, 721
31. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. 1978, 17, 569
32. For a metalation of DMAP with a potassium zincate, see: Conway, B.; Graham, D. V.; Hevia, E.; Kennedy, A. R.; Klett, J.; Mulvey, R. E. Chem. Commun. 2008, 2638
33. 11B NMR spectroscopy (ref 6).
34. 2, the cross-coupling proceeds in lower yields.
35. Molander, G. A.; Canturk, B. Angew. Chem., Int. Ed. 2009, 48, 9240
36. Farina, V.; Baker, S. R.; Benigni, D. A.; Sapino, C. Tetrahedron Lett. 1988, 29, 5739
37. Knochel, P.; Yeh, M.; Berk, S.; Talbert, J. J. Org. Chem. 1988, 53, 2390
38. Knochel, P.; Rao, S. A. J. Am. Chem. Soc. 1990, 112, 6146
39. Villiéras, J.; Rambaud, M. Org. Synth. 1988, 66, 220
40. Février, F. C.; Smith, E. D.; Comins, D. L. Org. Lett. 2005, 7, 5457
41. Wagner, F. F.; Comins, D. L. Eur. J. Org. Chem. 2006, 3562
42. Hoffmann, H. M. R.; Frackenpohl, J. Eur. J. Org. Chem. 2004, 4293
43. Kaufman, T. S.; Rúveda, E. A. Angew. Chem., Int. Ed. 2005, 44, 854
44. Seeman, J. I. Angew. Chem., Int. Ed. 2007, 46, 1378
45. Laurie, W. A.; Mc Hale, D.; Saag, K. Tetrahedron 1986, 42, 3711
46. Coors, C.; Matusch, R. Arch. Pharm. 1989, 322, 817
47. Johansson, C. C. C.; Bremeyer, N.; Ley, S. V.; Owen, D. R.; Smith, S. C.; Gaunt, M. J. Angew. Chem., Int. Ed. 2006, 45, 6024
48. Hintermann, L.; Schmitz, M.; Englert, U. Angew. Chem., Int. Ed. 2007, 46, 5164
49. Besenius, P.; Cormack, P. A. G.; Liu, J.; Otto, S.; Sanders, J. K. M.; Sherrington, D. C. Chem.-Eur. J. 2008, 14, 9006
50. Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7685
51. Dong, Z.; Clososki, G. C.; Wunderlich, S. H.; Unsinn, A.; Li, J.; Knochel, P. Chem.-Eur. J. 2009, 15, 457