Asymmetrie intermodular Pauson-Khand reaction of symmetrically substituted alkynes

Organic Letters

Volumn 11, Issue 19, 2009, Pages 4346-4349

  Ji, Yining ^a   Riera, Antoni ^a   Verdaguer, Xavier ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; COBALT; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; LIGAND; N PHOSPHINO P TOLYLSULFINAMIDE; N-PHOSPHINO-P-TOLYLSULFINAMIDE; ORGANOMETALLIC COMPOUND; SULFONAMIDE; TOLUENE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; COBALT; CYCLOPENTANES; LIGANDS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; SULFONAMIDES; TOLUENE;

EID: 70350150827     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901728r     Document Type: Article

References (31)

1. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977.
2. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Chem. Commun. 1971, 36.
3. Gibson, S. E.; Lewis, S. E.; Loch, J. A.; Steed, J. W.; Tozer, M. J. Organometallics 2003, 22, 5382.
4. Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797.
5. Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771.
6. Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852.
7. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026.
8. For selected reviews on the PKR, see: (a) Shibata, T. Adv. Synth. Catal. 2006, 348, 2328.
9. (b) Gibson, S. E.; Mainolfi, N. Angew. Chem., Int. Ed. 2005, 44, 3022.
10. (c) Laschat, S.; Becheanu, A.; Bell, T.; Baro, A. Synlett 2005, 2547.
11. (d) Bonaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
12. (e) Blanco-Urgoiti, J.; Anorbe, L.; Pérez-Serrano, L.; Dominguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2004, 33, 32.
13. (f) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800.
14. (g) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263.
15. (h) Pericas, M. A.; Balsells, J.; Castro, J.; Marchueta, I.; Moyano, A.; Riera, A.; Vazquez, J.; Verdaguer, X. Pure Appl, Chem. 2002, 74, 167.
16. (a) Bladon, P.; Pauson, P. L.; Branner, H.; Eder, R. J. Oreanomet. Chem. 1988, 355, 449.
17. (b) Hay, A. M.; Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Oreanometallics 1995, 14, 4986.
18. (c) Castro, J.; Moyano, A.; Pericas, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 2000, 122, 7944.
19. 2 diphosphines. However, double phosphorus coordination turns the resulting complexes completely unreactive; see: Derdau, V.; Laschat, S.; Dix, I.; Jones, P. G. Organometallics 1999, 18, 3859.
20. Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. J. Am. Chem. Soc. 2000, 122, 10242.
21. Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868.
22. Verdaguer, X.; Lledó, A.; López-Mosquera, C.; Maestro, M. A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2004, 69, 8053.
23. Solà, J.; Riera, A.; Verdaguer, X.; Maestro, M. A. J. Am. Chem. Soc. 2005, 127, 13629.
24. Solà, J.; Revés, M.; Riera, A.; Verdaguer, X. Angew. Chem., Int. Ed. 2007, 46, 5020.
25. Revés, M.; Achard, T.; Solà, J.; Riera, A.; Verdaguer, X. J. Org. Chem. 2008, 73, 7080.
26. 2, Pd/C, MeOH). The dihydro derivative provided single crystals suitable for X-ray analysis. The absolute configuration was determined by the anomalous dispersion method.
27. For a review on sulfoxide-metal bonding, see: Calligaris, M. Coord. Chem. Rev. 2004, 248, 351.
28. (a) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289.
29. (b) Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A.; Bernardes, V.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 1994, 116, 2153.
30. (c) Montenegro, E.; Poch, M.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 1998, 39, 335.
31. (d) Verdaguer, X.; Vazquez, J.; Fuster, G.; Bernardes-Genisson, V.; Greene, A. E.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037.