Rh(I)-catalyzed carbonylative ring opening of diazabicycles with acyl anion equivalents

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5365-5367

  Menard, Frederic ^a   Weise, Christian Frederik ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; AZABICYCLO DERIVATIVE; KETONE; RHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANIONS; AZABICYCLO COMPOUNDS; CATALYSIS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; RHENIUM;

EID: 38349195107     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7022054     Document Type: Article

References (51)

1. (a) Harada, Y.; Nakanishi, J.; Fujihara, H.; Tobisu, M.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2007, 129, 5766.
2. (b) Tanaka, K.; Shibata, Y.; Suda, T.; Hagiwara, Y.; Hirano, M. Org. Lett. 2007, 9, 1215.
3. (c) Hong, Y. T.; Barchuk, A.; Krische, M. J. Angew. Chem., Int. Ed. 2006, 45, 6885.
4. (d) Moxham, G. L.; Randell-Sly, H. E.; Brayshaw, S. K.; Woodward, R. L.; Weller, A. S.; Willis, M. C. Angew. Chem., Int. Ed. 2006, 45, 7618.
5. (e) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078.
6. (f) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10296.
7. (a) Beller, M.; Krauter, J. G. E. In Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; Cornils, B., Herrmann, W. A., Eds; Wiley-VCH: New York, 2002. Palladium:
8. b) Zeni, G.; Larock, R. L. Chem. Rev. 2006, 106, 4644. Cobalt:
9. (c) Struebing, D.; Beller, M. Top. Organomet. Chem. 2006, 18, 165.
10. (d) Klingler, R. J.; Chen, M. J.; Rathke, J. W.; Kramarz, K. W. Organometallics 2007, 26, 352.
11. For Pauson-Khand reactions: (a) Struebing, D.; Beller, M. Top. Organomet. Chem. 2006, 18, 165.
12. (b) Bayden, A. S.; Brummond, K. M.; Jordan, K. D. Organometallics 2006, 25, 5204.
13. (c) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948. For hydroformylation reactions:
14. (d) Thomas, P. J.; Axtell, A. T.; Klosin, J.; Peng, W.; Rand, C. L.; Clark, T. P.; Landis, C. R.; Abboud, K. A. Org. Lett. 2007, 9, 2665.
15. (e) Kuil, M.; Soltner, T.; van Leeuwen, P. W. N. M.; Reek, J. N. H. J. Am. Chem. Soc. 2006, 128, 11344.
16. (f) Huang, J.; Bunel, E.; Allgeier, A.; Tedrow, J.; Storz, T.; Preston, J.; Correll, T.; Manley, D.; Soukup, T.; Jensen, R.; Syed, R.; Moniz, G.; Larsen, R.; Martinelli, M.; Reider, P. J. Tetrahedron Lett. 2005, 46, 7831. For silylformylation:
17. (g) Zacuto, M. J.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 8587. For C-H functionalization:
18. (h) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Ishii, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
19. (a) Cortez, G. A.; Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 4534.
20. (b) Cook, M. J.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 9302.
21. (c) Johnson, J. B.; Bercot, E. A.; Williams, C. M.; Rovis, T. Angew. Chem., Int. Ed. 2007, 46, 4514.
22. (d) Arai, K.; Lucarini, S.; Salter, M. M.; Ohta, K.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 8103.
23. (e) Berlin, J. M.; Goldberg, S. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 7591.
24. (f) Bournaud, C.; Falciola, C.; Lecourt, T.; Rosset, S.; Alexakis, A.; Micouin, L. Org. Lett. 2006, 8, 3581.
25. (g) Cabrera, S.; Arrayas, R. G.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 2005, 127, 17938.
26. For a prime example of Rh-catalyzed desymmetrization: (a) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48. See also:
27. (b) McManus, H. A.; Fleming, M. J.; Lautens, M. Angew. Chem., Int. Ed 2007, 46, 433.
28. (c) Tseng, N.-W.; Mancuso, J.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 5338.
29. (d) Menard, F.; Chapman, T. M.; Dockendorff, C.; Lautens, M. Org. Lett. 2006, 8, 4569.
30. Evans, P. A. In Modern Rhodium-Catalyzed Organic Reactions; Wiley-VCH: Weinheim, Germany, 2005.
31. This concept was recently recognized by Castanet to generate 1,4-diketones from enones: (a) Chochois, H.; Sauthier, M.; Maerten, E.; Castanet, Y.; Mortreux, A. Tetrahedron 2006, 62, 11740.
32. (b) Askin, O.; Dege, N.; Artok, L.; Tuerkmen, H.; Cetinkaya, B. Chem. Commun. 2006, 3187.
33. (c) Sauthier, M.; Castanet, Y.; Mortreux, A. Chem. Commun. 2004, 1520.
34. For carbonyl insertion/extrusion studies, see: (a) Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1674.
35. (b) Beck, C. M.; Rathmill, S. E.; Park, Y. J.; Chen. J.; Crabtree, R. H.; Liable-Sands, L. M.; Rheihold, A. L. Organometallics 1999, 18, 5311.
36. Pineschi, M.; Del Moro, F.; Crotti, P.; Macchia, F. Org. Lett. 2005, 7, 3605.
37. Racemic: (a) John, J.; Sajisha, V. S.; Mohanlal, S.; Radhakrishnan, K. V. Chem. Commun. 2006, 3510. Asymmetric:
38. (b) Bertolini, F.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 2006, 47, 9173.
39. (c) Menard, F.; Lautens, M. Unpublished work.
40. Luna, A. P.; Cesario, M.; Bonin, M.; Micouin, L. Org. Lett. 2003, 5, 4771.
41. Diels, O.; Bolm, J. H.; Knoll, W. Justus Liebigs Ann. Chem. 1925, 443, 242. 1b is a free-flowing powder, making for easy handling. Its preparation on scale is convenient, involving simple filtration of the reaction mixture to obtain analytically pure material.
42. (a) Poulsen, T. B.; Alemparte, C; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 11614.
43. (b) Ding, H.; Friestad, G. K. Org. Lett. 2004, 6, 637.
44. (c) Evans, D. A.; Britton, T. C.; Dorow. R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525.
45. When the same reaction was conducted under an argon atmosphere, 2a was obtained in >70% yield (see ref 10c). This observation suggests that when CO is present, it coordinates to Rh(I) preferentially to 1, and that only when the acyl rhodium species is formed is the alkene 1 allowed to bind and react.
46. Lautens, M.; Dockendorff, C. Org. Lett. 2003, 5, 3695.
47. Such a synthesis of symmetrical ketones was reported with organomercurials and rhodium under a CO atmosphere: Larock, R. C.; Hershberger, S. S. J. Org. Chem. 1980, 45, 3840.
48. Even after heating, the mass balance consisted mainly of unreacted starting material.
49. Though the arylation product 2 is formed with significant enantiomeric enrichment under the same conditions (89:11 er), the acylated product 3 was nearly racemic (55:45 er).
50. This phenomenon was also observed by others (see ref 3f).
51. In preliminary experiments, oxabicycle 19 reacted, but only the aromatized ketone 20 was isolated: