Carbocupration of diethyl 1-alkynyl phosphonates: Stereo- and regioselective synthesis of 1,2,2-trisubstituted vinyl phosphonates

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2950-2953

  Gil, Jun Mo ^a   Oh, Dong Young ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; ORGANOMETALLIC COMPOUND; PHOSPHONIC ACID DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; GAS CHROMATOGRAPHY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0000632690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982123w     Document Type: Article

References (37)

1. For reviews on organocopper(I) chemistry, see (a) Normant, J. F. Synthesis 1972, 63.
2. (b) Posner, G. H. Org. React. 1972, 19, 1.
3. (c) Jukes, A. E. Adv. Organomet, Chem. 1975, 12, 215.
4. (d) Posner, G. H. Org. React. 1978, 22, 253.
5. (e) Normant, J. F.; Alexakis, A. Synthesis 1981, 841.
6. (a) Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851.
7. (b) Siddall, J. B.; Biskup, M.; Fried, J. H. Ibid. 1969, 91, 1853.
8. (c) Klein, J.; Turkel, R. M. Ibid. 1969, 91, 6189.
9. (d) Klein, J.; Aminadav, N. J. Chem. Soc. C 1970, 1380.
10. (a) Vermeer, P.; Meijer, J.; Eylander, C. Recl. Trav. Chim. Pays-Bas 1974, 93, 240.
11. (b) Truce, W. E.; Lusch, M. J. J. Org. Chem. 1974, 39, 3174.
12. (c) Truce, W. E.; Lusch, M. J. Ibid. 1978, 43, 2252.
13. (d) Fiandanese, V.; Marchese, G.; Naso, F. Tetrahedron Lett. 1978, 5131.
14. (e) Meijer, J.; Vermeer, P. Red. Trav. Chim. Pays-Bas 1975, 94, 14.
15. Aguiar, A. M.; Smiley Irelan, J. R. J. Org. Chem. 1969, 34, 4030.
16. For reviews on vinylphosphonates and their synthetic applications, see Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
17. (a) Engel, R. Chem. Rev. 1977, 77, 349.
18. (b) Breaker. R. R.; Gough, G. R.; Gilham, P. T. Biochemistry 1993, 32, 9125.
19. (c) Harnden, M. R.; Parkin, A.; Parratt, M. J.; Perkins, R. M. J. Med. Chem. 1993, 36, 1345.
20. (a) Tavs, P.; Weitkamp, H. Tetrahedron 1970, 26, 5529.
21. (b) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
22. Axelrad, G.; Laosooksathit, S.; Engel, R. J. Org. Chem. 1981, 46, 5200.
23. Lee, C.-W.; Hong, J. E.; Oh, D. Y. J. Org. Chem. 1995, 60, 7027.
24. Gil, J. M.; Sung, J. W.; Park, C. P.; Oh, D. Y. Synth. Commun. 1997, 27, 3171.
25. (a) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras J. Bull. Soc. Chim. Fr. 1974, 1656.
26. (b) Weatmijze, H.; Meijer, J.; Bos, H. J. T.; Vermeer, P. Recl. Trav. Chim. Pays-Bas 1976, 95, 299, 304.
27. (c) Marfat, A.; McQuirk, P. R.; Helquist, P. J. Org. Chem. 1979, 44, 3888.
28. (a) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785.
29. (b) For reviews on vinylic selenides and tellurides - preparation, reactivity, and their synthetic applications, see Comasseto, J. V.; Ling, L. W.; Petragnani, N.; Stefani, H. A. Synthesis 1997, 373.
30. Lee, C.-W.; Koh, Y. J.; Oh, D. Y. J. Chem. Soc., Perkin Trans. 1 1994, 717.
31. (a) Comasseto, J. V.; Petragnani, N. J. Organomet. Chem. 1978, 152, 295.
32. (b) Mikolajczyk, M.; Grzejszczak, S.; Korbacz, K. Tetrahedron Lett. 1981, 22, 3097.
33. (c) Khan, N.; Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Perkin Trans. 1 1991, 865.
34. (d) Shin, W. S.; Lee, K.; Oh, D. Y. Bull. Korean Chem. Soc. 1996, 17, 981.
35. (a) Ahlbrecht, H.; Farnung, W.; Simon, H. Chem. Ber. 1984, 117, 2622.
36. (b) Binder, J.; Zbiral, E. Tetrahedron Lett. 1986, 27, 5829.
37. (c) Ager, D. Org. React. 1990, 38, 1-223.