Preparation of functionalized cyclic enol phosphates by halogen-magnesium exchange and directed deprotonation reactions

Journal of Organic Chemistry

Volumn 75, Issue 13, 2010, Pages 4365-4375

  Piller, Fabian M ^a   Bresser, Tomke ^a   Fischer, Markus K R ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; ALLYL BROMIDE; CROSS COUPLING REACTIONS; DEPROTONATION REACTION; ELECTROPHILES; EXCHANGE REACTION; FUNCTIONALIZED; MAGNESIUM REAGENTS;

AMIDES; BROMINE COMPOUNDS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; MAGNESIUM; PALLADIUM;

PHOSPHATES;

BROMIDE; CAMPHOR DERIVATIVE; ELECTROPHILE; ENOLASE; HALOGEN; MAGNESIUM; PALLADIUM;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CROSS COUPLING REACTION; DEPROTONATION REACTION;

CAMPHOR; CATALYSIS; CYCLOPARAFFINS; HALOGENS; INDICATORS AND REAGENTS; MAGNESIUM; PHOSPHATES; PROTONS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77954136756     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100763f     Document Type: Article

References (45)

1. Lichtenthaler, F. W. Chem. Rev. 1961, 61, 607
2. Ding, Y.; Huang, X. Heteroatom Chem. 2003, 14, 304
3. Stowell, J. K.; Widlanski, T. S. J. Am. Chem. Soc. 1994, 116, 789
4. Widlanski, T. S. US Patent 5,714,361.
5. Takai, K.; Sato, M.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1984, 57, 108
6. Cahiez, G.; Gager, O.; Habiak, V. Synthesis 2008, 16, 2636
7. Miller, J. A. Tetrahedron Lett. 2002, 43, 7111
8. Larsen, U. S.; Martiny, L.; Begtrup, M. Tetrahedron Lett. 2005, 46, 4261
9. Calogeropoulou, T.; Hammond, G. B.; Wiemer, D. F. J. Org. Chem. 1987, 52, 4185
10. Baker, T. J.; Wiemer, D. F. J. Org. Chem. 1998, 63, 2613
11. Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333
12. Krasovskiy, A.; Straub, B. F.; Knochel, P. Angew. Chem., Int. Ed. 2005, 45, 159
13. Piller, F. M.; Appukkuttan, P.; Gavryushin, A.; Helm, M.; Knochel, P. Angew. Chem., Int. Ed. 2008, 47, 6802
14. Piller, F. M.; Metzger, A.; Schade, M. A.; Haag, B. A.; Gavryushin, A.; Knochel, P. Chem. - Eur. J. 2009, 15, 7192
15. Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 2958
16. Clososki, G. C.; Rohbogner, C. J.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7681
17. Rohbogner, C. J.; Clososki, G. C.; Knochel, P. Angew. Chem., Int. Ed. 2008, 47, 1503
18. Rohbogner, C. J.; Wirth, S.; Knochel, P. Org. Lett. 2010, 12, 1984
19. Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 6040
20. Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7685
21. Chen, Y.-H.; Knochel, P. Angew. Chem., Int. Ed. 2008, 47, 7648
22. Chen, Y.-H.; Sun, M.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 2236
23. Aluminum: Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 1501
24. Blümke, T. D.; Chen, Y.-H.; Knochel, P. Nature Chem. 2010, 2, 313
25. Manganese: Wunderlich, S. H.; Kienle, M.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 7256
26. Iron: Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 9717
27. Wunderlich, S. H.; Knochel, P. Chem. - Eur. J. 2010, 16, 3304
28. Ren, H.; Krasovskiy, A.; Knochel, P. Org. Lett. 2004, 6, 4215
29. Ren, H.; Krasovskiy, A.; Knochel, P. Chem. Commun. 2005, 543
30. Katritzky, A. R.; Yannokopoulou, K.; Kuzmierkiewicz, W.; Aurrecoechea, J. M.; Palenik, G. J.; Koziol, A. E.; Szczesniak, M. J. Chem. Soc., Perkin Trans. 1 1987, 12, 2673
31. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390
32. Negishi, E. Acc. Chem. Res. 1982, 15, 340
33. Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298
34. Zeng, X.; Quian, M.; Hu, Q.; Negishi, E. Angew. Chem., Int. Ed. 2004, 43, 2259
35. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 112, 9585
36. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905
37. Klement, I.; Rottländer, M.; Tucker, C. E.; Majid, T. N.; Knochel, P.; Venegas, P.; Cahiez, G. Tetrahedron 1996, 52, 7201
38. Oppolzer, W. Tetrahedron 1987, 43, 1969
39. Chelucci, G. Chem. Soc. Rev. 2006, 35, 1230
40. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685
41. Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 116, 1907
42. 2/tfp did not lead to the corresponding cross-coupling products when aryl bromides were used instead of aryl iodides.
43. Vashchenko, V.; Kutulya, L.; Krivoshey, A. Synthesis 2007, 14, 2125
44. Rohbogner, C. J.; Wagner, A. J.; Clososki, G. C.; Knochel, P. Org. Synth. 2009, 86, 374
45. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001