Transition-metal-catalyzed chemoselective methylenation of dicarbonyl substrates

Journal of Organic Chemistry

Volumn 73, Issue 17, 2008, Pages 6828-6830

  Lebel, Hélène ^a   Davi, Michaël ^a   Stokłosa, Grzegorz T ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHEMICAL REACTIONS; COPPER; HYDROCARBONS; ORGANIC COMPOUNDS; RHODIUM;

CHEMICAL EQUATIONS; METHYLENATION; TRIPHENYL PHOSPHINES;

TRANSITION METALS;

2 PROPANOL; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; COPPER; DIAZONIUM COMPOUND; KETONE DERIVATIVE; RHODIUM; TRANSITION ELEMENT; TRIPHENYLPHOSPHINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION;

2-PROPANOL; ALDEHYDES; CATALYSIS; COPPER; DIAZOMETHANE; KETONES; METHYLATION; MODELS, CHEMICAL; ORGANOPHOSPHORUS COMPOUNDS; RHODIUM; TRANSITION ELEMENTS; TRIMETHYLSILYL COMPOUNDS;

EID: 51549085438     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800777w     Document Type: Article

References (32)

1. Saito, S.; Yamamoto, H. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; pp 33-67.
2. (a) Asao, N.; Asano, T.; Yamamoto, Y. Angew Chem., Int. Ed. 2001, 40, 3206-3208, and references therein.
3. (b) Yamamoto, H.; Maruoka, K.; Araki, Y. Tetrahedron Lett. 1988, 29, 3101-3104.
4. Selected examples: (a) Olpp, T.; Bruckner, R. Angew. Chem., Int. Ed. 2006, 45, 4023-4027.
5. (b) Trost, B. M.; Dirat, O.; Gunzner, J. L. Angew. Chem., Int. Ed. 2002, 41, 841-843.
6. (c) Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157-3160.
7. (d) Kahnberg, P.; Lee, C. W.; Grubbs, R. H.; Sterner, O. Tetrahedron 2002, 58, 5203-5208.
8. (e) Oesterreich, K.; Klein, I.; Spitzner, D. Synlett 2002, 1712-1714.
9. (f) Faure, S.; Piva, O. Tetrahedron Lett. 2001, 42, 255-259.
10. (g) Kim, D.; Lee, J.; Chang, J.; Kim, S. Tetrahedron 2001, 57, 1247-1252.
11. (h) Colombo, M. I.; Zinczuk, J.; Mischne, M. P.; Ruveda, E. A. Tetrahedron: Asymmetry 2001, 12, 1251-1253.
12. (i) Nicolaou, K. C.; King, N. P.; Finlay, M. R. V.; He, Y.; Roschangar, F.; Vourloumis, D.; Vallberg, H.; Sarabia, F.; Ninkovic, S.; Hepworth, D. Bioorg. Med. Chem. 1999, 7, 665-697.
13. (j) Hsu, P.-Y.; Lee, Y.-C.; Liao, C.-C. Tetrahedron Lett. 1998, 39, 659-662.
14. (k) Paquette, L. A.; Heidelbaugh, T. M. Synthesis 1998, 495-508.
15. (l) Evans, D. A.; Trotter, B. W.; Cote, B.; Coleman, P. J.; Dias, L. C.; Tyler, A. N. Angew. Chem., Int. Ed. 1997, 36, 2744-2747.
16. (m) Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977.
17. (a) Matsubara, S.; Oshima, K.; Utimoto, K. J. Organomet. Chem. 2001, 617, 39-46.
18. (b) Matsubara, S.; Mizuno, T.; Otake, Y.; Kobata, M.; Utimoto, K.; Takai, K. Synlett 1998, 1369-1371.
19. (c) Okazoe, T.; Hibino, J.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581-5584.
20. (a) Lebel, H.; Paquet, V.; Proulx, C. Angew. Chem., Int. Ed. 2001, 40, 2887-2890.
21. (b) Grasa, G. A.; Moore, Z.; Martin, K. L.; Stevens, E. D.; Nolan, S. P.; Paquet, V.; Lebel, H. J. Organomet. Chem. 2002, 658, 126-131.
22. (c) Lebel, H.; Paquet, V. Org. Lett. 2002, 4, 1671-1674.
23. (d) Lebel, H.; Guay, D.; Paquet, V.; Huard, K. Org. Lett. 2004, 6, 3047-3050.
24. (e) Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 320-328.
25. (f) Paquet, V.; Lebel, H. Synthesis 2005, 1901-1905.
26. (g) Lebel, H.; Davi, M.; Diez-Gonzalez, S.; Nolan, S. P. J. Org. Chem. 2007, 72, 144-149.
27. For recent examples of application in total synthesis, see: (a) Kwon, M. S.; Woo, S. K.; Na, S. W.; Lee, E. Angew. Chem., Int. Ed. 2008, 47, 1733-1735.
28. (b) Zhang, H.; Reddy, M. S.; Phoenix, S.; Deslongchamps, P. Angew. Chem., Int. Ed. 2008, 47, 1272-1275.
29. (c) Lebel, H.; Parmentier, M. Org. Lett. 2007, 9, 3563-3566.
30. Lebel, H.; Paquet, V. Organometallics 2004, 23, 1187-1190.
31. Reitz, A. B.; Nortey, S. O.; Jordan, A. D., Jr.; Mutter, M. S.; Maryanoff, B. E. J. Org. Chem. 1986, 51, 3302-3308.
32. See Table S1 in Supporting Information for the methylenation reaction of ketoaldehyde 11 using various bases to generate the phosphorous ylide from methyltriphenylphosphonium bromide.