A New One-pot Synthesis of Alkynylphosphonates

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3873-3875

  Lera, Manuel ^a   Hayes, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038245524     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0066173     Document Type: Article

References (32)

1. (a) Shen, W. Synlett 2000, 737.
2. (b) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431.
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5. (e) Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551.
6. (f) Minato, A. J. Org. Chem. 1991, 56, 4052.
7. (g) Roush, W. R.; Moriarty, K. J.; Brown, B. B. Tetrahedron Lett. 1990, 31, 6509.
8. (h) Uenishi, J.; Kawahama, R.; Shiga, Y.; Yonemitsu, O. Tetrahedron Lett. 1996, 37, 6759.
9. (i) Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965.
10. Zapata, A. J.; Ruiz, J. J. Organomet. Chem. 1994, 479, C6.
11. Shen, W.; Wang, L. J. Org. Chem. 1999, 64, 8873.
12. Shen, W.; Thomas, S. A. Org. Lett. 2000, 2, 2857.
13. (a) Poss, A. J.; Belter, R. K. J. Org. Chem. 1987, 52, 4810.
14. (b) Chattha, M. S.; Aguiar, A. M. J. Org. Chem. 1973, 38, 2908. For use in synthesis, see: Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429.
15. (b) Chattha, M. S.; Aguiar, A. M. J. Org. Chem. 1973, 38, 2908. For use in synthesis, see: Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429.
16. Chattha, M. S.; Aguiar, A. M. J. Org. Chem. 1973, 38, 820.
17. Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950.
18. (a) Abbas, S.; Hayes, C. J. Tetrahedron Lett. 2000, 41, 4513.
19. (b) Abbas, S.; Hayes, C. J., Synlett 1999, 1124.
20. For an example of a Nickel-catalyzed monocoupling, see: Kazankova, M. A.; Trostyanskaya, I. G.; Lutsenko, S. V.; Beletskaya, I. P. Tetrahedron Lett. 1999, 40, 569.
21. When triethylamine was used in place of propylene oxide for this coupling, reduction of the 1,1-dibromo-1-alkene to the corresponding 1-bromo-1-alkene was observed. See: Abbas, S.; Hayes, C. J.; Worden, S. Tetrahedron Lett. 2000, 41, 3215 and references therein.
22. For preparation of 1,1-dibromo-1-alkenes see: Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745.
23. dppf = 1, 1′-Bis(diphenyl-phosphino)ferrocene.
24. 3, TFP, toluene, 100°C).
25. 31P, IR, MS, and/ or elemental analytical data.
26. TFP = tris(2-furyl)phosphine.
27. One exception to this was when trimethyl(phenyl)tin was used as the coupling partner. In this case alkyne formation was observed with a range of ligands, including TFP (see ref 3). The rate of transmetalation of the organostannane was proposed as the determining factor controling product selectivity in this process.
28. We believe the mechanism of this reaction to be similar to that proposed by Shen (see ref 3).
29. For synthesis, see ref 8b. The material was used as a 1:1 mixture of diastereoisomers at phosphorus.
30. The product 20 was produced as a 1:1 mixture of diasteroisomers at phosphorus, which were readily separable by column chromatography using silica gel and ethyl acetate/pentane/methanol (10:10:1) as eluant.
31. 2, EtOAc/pentane (3:1)) to afford 3 as a white solid (60 mg, 63%).
32. See refs 5, 6, and 7 for alternative methodology.