Synthesis of functionalised cyclohexadienes through addition of lithiated phosphine borane complexes to benzonitriles

Tetrahedron Letters

Volumn 43, Issue 52, 2002, Pages 9611-9614

  Andújar Sánchez, Carmen M ^a   Iglesias, Ma José ^a   López Ortiz, Fernando ^a  

^a UNIVERSITY OF ALMERÍA   (Spain)

Author keywords

Benzonitriles; Conjugate addition; Cyclohexadienes; Dearomatisation; Phosphine borane anions

Indexed keywords

ALKADIENE; ANION; BENZONITRILE; BORANE DERIVATIVE; CYCLOHEXADIENE; LITHIUM; PHOSPHINE; REAGENT; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; LITHIATION; PROTON TRANSPORT; SYNTHESIS;

EID: 0037164628     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02406-1     Document Type: Article

References (37)

1. Donohoe T.J., Garg R., Stevenson C.A. Tetrahedron: Asymmetry. 7:1996;317.
2. Schultz A.G. Chem. Commun. 1999;1263.
3. Brooks B.C., Gunnoe T.B., Harman W.D. Coord. Chem. Rev. 206:2000;3.
4. Smith P.L., Chordia M.D., Harman W.D. Tetrahedron. 57:2001;8203.
5. Valahovic M.T., Gunnoe T.B., Sabat M., Harman W.D. J. Am. Chem. Soc. 124:2002;3309.
6. Bartoli G. Acc. Chem. Res. 17:1984;109.
7. Maruoka K., Ito M., Yamamoto H. J. Am. Chem. Soc. 117:1995;9091.
8. Saito S., Shimada K., Yamamoto H., Marigorta E.M., Fleming I. Chem. Commun. 1997;1299.
9. Yamamoto H., Saito S. Pure Appl. Chem. 71:1999;239.
10. Saito S., Sone T., Shimada K., Yamamoto H. Synlett. 1999;81.
11. Saito S., Sone T., Murase M., Yamamoto H. J. Am. Chem. Soc. 122:2000;10216.
12. Ahmed A., Clayden J., Yasin S.A. Chem. Commun. 1999;231.
13. Clayden J., Tchabanenko K. Chem. Commun. 2000;317.
14. Clayden J., Menet C.J., Mansfield D.J. Org. Lett. 2:2000;4229.
15. Clayden J., Tchabanenko K., Yasin S.A., Turnbull M.D. Synlett. 2001;302.
16. Clayden J., Menet C.J., Mansfield D.J. Chem. Commun. 2002;38.
17. Clayden J., Purewal S., Helliwell M., Mantell S.J. Angew. Chem., Int. Ed. 41:2002;1049.
18. Nishiwaki K., Ogawa T., Matsuo K. Angew. Chem., Int. Ed. 41:2002;484.
19. Crandall J.K., Ayers T.A. J. Org. Chem. 57:1992;2993.
20. Padwa A., Filipkowski M.A., Kline D.N., Murphree S., Yeske P.E. J. Org. Chem. 58:1993;2061.
21. Aggarwal V.K., Ferrara M. Org. Lett. 2:2000;4107.
22. Aggarwal V.K., Alonso E., Ferrara M., Spey S.E. J. Org. Chem. 67:2002;2335.
23. Fernández I., López Ortiz F., Tejerina B., García Granda S. Org. Lett. 3:2001;1339.
24. Fernández I., López-Ortiz F., Velázquez A., García-Granda S. J. Org. Chem. 67:2002;3852.
25. Cook L.S., Wakefield B.J. J. Chem. Soc., Perkin Trans. 1. 1980;2392.
26. Armstrong D.R., Clegg W., MacGregor M., Mulvey R.E., O'Neil P.A. J. Chem. Soc., Chem. Commun. 1993;608.
27. Chastrette M., Axiotis G., Gauthier R. Tetrahedron Lett. 1977;23.
28. Bertus P., Szymoniak J. J. Org. Chem. 67:2002;3965.
29. Andújar C.M., Iglesias M.J., López-Ortiz F. Tetrahedron Lett. 43:2002;2565.
30. We have observed an analogous behaviour in lithiated (N-methoxycarbonyl)phosphazenes. (a) Álvarez-Gutiérrez, J. M.; López-Ortiz, F. Tetrahedron Lett. 1996, 37, 2841; (b) Andújar, C. M.; Pérez-Álvarez, I.; López-Ortiz, F. Tetrahedron 2002, 58, 2569.
31. We have observed an analogous behaviour in lithiated (N-methoxycarbonyl)phosphazenes. (a) Álvarez-Gutiérrez, J. M.; López-Ortiz, F. Tetrahedron Lett. 1996, 37, 2841; (b) Andújar, C. M.; Pérez-Álvarez, I.; López-Ortiz, F. Tetrahedron 2002, 58, 2569.
32. 2Cl (1c). Aguiar, A. M.; Beisler, J.; Mills, A. J. Org. Chem. 1962, 27, 1001.
33. In the absence of HMPA the metalation required 2 h. See: Imamoto, T.; Kusumoto, T.; Suzuki, N.; Sato, K. J. Am. Chem. Soc. 1985, 107, 5303.
34. For a recent review on the synthesis and applications of phosphine borane complexes, see: Brunel, J. M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 178-180, 665.
35. ++1).
36. PC=5.4 Hz. This rearrangement has been previously observed in the analogous reaction of lithium N-methoxycarbonylphosphazenes. Barluenga, J.; Ferrero, M.; López-Ortiz, F.; Palacios, F. J. Chem. Soc., Perkin Trans. 1 1989, 615.
37. Chupakhin O.N., Charushin V.N., van der Plas H.C. Nucleophilic Aromatic Substitution of Hydrogen. 1994;Academic Press, San Diego.