Tandem Aminocarbonylation/ Pauson-Khand Reaction of Haloacetylenes

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1981-1984

  Balsells, Jaume ^a   Moyano, Albert ^a   Riera, Antoni ^a   Pericàs, Miquel A ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000435969     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991145h     Document Type: Article

References (28)

1. For leading references, see: (a) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II: Hegedus, L. S., Ed.; Elsevier: Oxford, 1995; Vol. 12, pp 685-702.
2. (b) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207-214.
3. For recent reviews, see: (a) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341.
4. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S. Ed.; Elsevier: Oxford, 1995; Vol. 12, pp 703-739.
5. Verdaguer. X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037-7052 and references therein.
6. Montenegro, E.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1998, 39, 335-338 and references therein.
7. Montenegro, E.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J. F. Tetrahedron: Asymmetry 1999, 10, 457-471.
8. Fonquerna, S.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Am. Chem. Soc. 1997, 119, 10225-10226 and references therein.
9. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289-5292.
10. 13C chemical shift correlations.
11. Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207.
12. (a) Hübel, W.; Merényi, R. Chem. Ber. 1963, 96, 930-943.
13. (b) Dickson, R. S.; Tailby, G. R. Aust. J. Chem. 1969, 22, 1143-1148.
14. Attempts to grow a single crystal from solutions of 4 have failed. Work aimed to the preparation of a crystalline analogue is actively pursued.
15. For IR spectra of acylmetal complexes, see, for instance: van Asselt, R.; Gielens, E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier: C. J. J. Am. Chem. Soc. 1994, 116, 977-985.
16. 13C NMR, IR, MS, and HRMS.
17. An authentic sample of this complex, prepared from phenylpropynoyl chloride and octacarbonyl dicobalt exhibited a distinct IR spectrum and did not react with NBD to afford 3.
18. In could be established that 4, isolated by column chromatography, does not react with NBD at that temperature to yield any cyclopentenone adduct.
19. The calculations were performed with the ADF 2.0.1 code, with the II(DZ) small core basis set, using the VWN local exchange correlation potential with Perdew-Wang 91 exchange and correlation corrections: (a) Baerends, E. J.; Ellis, D. E.; Ros, P. E. Chem. Phys. 1973, 2, 41-51.
20. (b) Versluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322-328.
21. (c) Fan, L.; Ziegler, T. J. Chem. Phys. 1991, 95, 7401-7408.
22. (d) teVelde, G.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84-98.
23. SPARTAN, version 4.1.1, Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612.
24. Sugihara, T.; Okada, Y.; Yamaguchi, M.; Nishizawa, M. Synlett 1999, 768-770.
25. 3 prop-2-ynyl complexes, see: Shiu, L. H.; Wang, S.-L.; Wu, M.-J.; Liu, R.-S. Chem. Commun. 1997, 2055-2056.
26. When these conditions are applied to complex 4 alone, no aminocarbonylation is observed at all.
27. The 3-azabicyclo[3.3.0]octan-7-one system has been used as a precursor to α-kainic acid (Yoo, S.; Lee, S. H. J. Org. Chem. 1994, 59, 6968-6972) and to serotonergic agents (Becker, D. P.; Flynn, D. L. Tetrahedron 1993, 49, 5047-5054).
28. The 3-azabicyclo[3.3.0]octan-7-one system has been used as a precursor to α-kainic acid (Yoo, S.; Lee, S. H. J. Org. Chem. 1994, 59, 6968-6972) and to serotonergic agents (Becker, D. P.; Flynn, D. L. Tetrahedron 1993, 49, 5047-5054).