Chemoselectivity in the rhodium(II) acetate catalysed decomposition of α-diazo-β-keto-γ,δ-alkenyl-δ-aryl compounds: Aromatic C-H insertion reaction or Wolff rearrangement-electrocyclization

Tetrahedron

Volumn 52, Issue 31, 1996, Pages 10455-10472

  Collomb, Didier ^a   Chantegrel, Bernard ^a   Deshayes, Christian ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 NAPHTHOIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605908     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00581-9     Document Type: Article

References (54)

1. 1. For reviews, see: a) Doyle, M.P. Chem. Rev. 1986, 86, 919-939.
2. b) Maas, G. Top. Curr. Chem. 1987, 137, 75-253.
3. c) Adams, J.; Spero, D.M. Tetrahedron 1991, 47, 1765-1808.
4. d) Padwa, A.; Krumpe, K.E. Tetrahedron 1992, 48, 5385-5453.
5. e) Shapiro, E.A.; Dyatkin, A.B.; Nefedov, O.M. Russ. Chem. Rev. 1993, 62, 447-472.
6. f) Ye, T.; McKervey, M.A. Chem. Rev. 1994, 94, 1091-1160.
7. g) Padwa, A.; Austin, D.J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797-1815.
8. 2. a) Taylor, E.C.; Davies, H.M.L. Tetrahedron Lett. 1983, 24, 5453-5456.
9. b) Matsumoto, M.; Watanabe, N.; Kobayashi, H. Heterocycles 1987, 26, 1479-1482.
10. c) Hashimoto, S.; Watanabe, N.; Ikegami, S. J. Chem. Soc., Chem. Comm. 1992, 1508-1510.
11. 3. Nakatani, K. Tetrahedron Lett. 1987, 28, 165-166.
12. 4. Hrystsak, M.; Durst, T. J. Chem. Soc., Chem. Comm. 1987, 1150-1151.
13. 5. a) Doyle, M. P.; Shanklin, M.S.; Pho, H.Q.; Mahapatro, S.N. J. Org. Chem. 1988, 53, 1017-1022.
14. b) Etkin, N.; Babu, S.D.; Fooks, C.J.; Durst, T. J. Org. Chem. 1990, 55, 1093-1096.
15. c) Wee, A.G.H.; Liu, B.; Zhang, L. J. Org. Chem. 1992, 57, 4404-4414.
16. d) Brown, D.S.; Elliot, M.C.; Moody, C.J.; Mowlem, T.J.; Marino, Jr., J.P.; Padwa, A. J. Org. Chem. 1994, 59, 2447-2455.
17. e) Miah, S.; Slawin, A.M.Z.; Moody, C.J.; Sheehan, S.M.; Marino, Jr., J.P.; Semones, M.A.; Padwa, A.; Richards, I.C. Tetrahedron 1996, 52, 2489-2514.
18. 6. Hrystsak, M.; Etkin, N.; Durst, T. Tetrahedron Lett. 1986, 27, 5679-5682.
19. 7. a) Andriamiadanarivo, R.; Pujol, B.; Chantegrel, B.; Deshayes, C.; Doutheau, A. Tetrahedron Lett. 1993, 34, 7923-7924.
20. b) Chen, Y. P.; Chantegrel, B.; Deshayes, C. Heterocycles, 1995, 41, 175-186.
21. c) Collomb, D.; Deshayes, C.; Doutheau, A. Tetrahedron 1996, 52, 6665-6684.
22. 8. The spectral comparison of the naphthol 5a with its isomer 3a obtained under thermal conditions permitted us to confirm their structures.
23. 9. Taber, D.F.; Ruckle, Jr., R.E. J. Am. Chem. Soc. 1986, 108, 7686-7693.
24. 10. Adams, J.; Poupart, M.-A.; Grenier, L.; Schaller, C.; Ouimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749-1752.
25. 11. Doyle, M.P.; Taunton, J.; Pho, H.Q. Tetrahedron Lett. 1989, 30, 5397-5400.
26. 12. Ceccherelli, P.; Curini, M.; Marcotullio, M.C.; Rosati, O.; Wenkert, E. J. Org. Chem. 1991, 56, 7065-7070.
27. 13. Spero, D.M.; Adams, J. Tetrahedron Lett. 1992, 33, 1143-1146.
28. 14. Hashimoto, S.; Watanabe, N.; Ikegami, S. Tetrahedron Lett. 1992, 33, 2709-2712.
29. 15. Doyle, M. P.; Shanklin, M.S.; Oon, S.-M.; Pho, H.Q.; Van der Heide, F.R.; Veal, W.R. J. Org. Chem. 1988, 53, 3384-3386.
30. 16. Ceccherelli, P.; Curini, M.; Marcotullio, M.C.; Rosati, O. Tetrahedron 1992, 48, 9767-9774.
31. 17. Moyer, M.P.; Feldman, P.L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223-5230.
32. 18. Cox, G.G.; Moody, C.J.; Austin, D.J.; Padwa, A. Tetrahedron 1993, 49, 5109-5126.
33. 19. Padwa, A.; Austin, D.J.; Hornbuckle, S.F. J. Org. Chem. 1996, 61, 63-72.
34. 20. Hon, Y.-S.; Chang, R.-C.; Chau, T.-Y. Heterocycles, 1990, 31, 1745-1750.
35. 21. Corbel, B.; Hernot, D.; Haelters, J.-P.; Sturtz, G. Tetrahedron Lett. 1987, 28, 6605-6608 and references cited therein.
36. 22. Rathke, M.W.; Bouhlel, E. Synth.Comm. 1990, 20, 869-875.
37. 23. Etemad-Moghadam, G.; Seyden-Penne, J. Bull. Soc. Chim. Fr. 1985, 448-454.
38. 24. Bergmann, E.D.; Solomonovici, A. Synthesis 1970, 183-189.
39. 25. Burton, D.J.; Koppes, W.M. J. Org. Chem. 1975, 40, 3026-3032.
40. 26. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1981, 46, 5340-5343.
41. 27. Koskinen, A.M.P.; Munoz, L. J. Chem. Soc., Chem. Commun. 1990, 652-653.
42. 28. Chemical shifts and coupling constants reported in Tables 2 and 3 were attributed as follows. The dimethyl hydroxynaphthalenephosphonates 3b and 5b served as reference compounds. Their H-3 and H-4 resonances were established by proton decoupling experiments. Attribution of the C-1 and C-2 resonances was evident because these carbons are bonded to the hydroxy and dimethylphosphono groups. CH COSY spectra permitted us to establish the H-3/C-3 and H-4/C-4 connectivities. Attribution of C-4a and C-8a resonances was based on the expected shielding effect produced by a hydroxy group on ortho and para carbons. All attributed resonances were consistent with the H-P and C-P coupling constants values observed in the NMR spectra. Chemical shifts and coupling constants of other compounds 3 and 5 were deduced on the basis of their spectral similarities with 3b and 5b.
43. CP = 2.7-3.0 Hz for C-4.
44. 1H FT NMR spectra, 1993, Edition I, vol. 2, spectra 1169 B (1-hydroxy-2-naphthoic acid) and 1169 C (2-hydroxy-1-naphthoic acid).
45. W = 0.083.
46. 32. The synthesis of a product described as 10c has been reported by Citterio, A.; Pesce, L.; Sebastiano, R.; Sand, R. Synthesis, 1990, 142-144. Several attempts to reproduce this synthesis failed.
47. 33. a) McKervey, M.A.; Tuladhar, S.M.; Twohig, M.F. J. Chem. Soc., Chem. Comm. 1984, 129-130.
48. b) Kennedy, M.; McKervey, M.A.; Maguire, A.R.; Tuladhar, S.M.; Twohig, M.F. J. Chem. Soc. Perkin Trans. 1, 1990, 1047-1054.
49. c) Duddeck, H.; Ferguson, G.; Kaitner, B.; Kennedy, M.; McKervey, M.A.; Maguire, A.R. J. Chem. Soc. Perkin Trans. 1, 1990, 1055-1063.
50. d) Kennedy, M.; McKervey, M.A. J. Chem. Soc. Perkin Trans. 1, 1991, 2565-2574.
51. 34. Motherwell, W.D.S.; Clegg, W. PLUTO: "Program for plotting molecular and crystal structures", University of Cambridge, England, 1978.
52. 35. Kirilov, M.; Petrov, G. Monatsh. 1972, 103, 1651-1660.
53. 36. Ooms, P.H.J.; Hartmann, W. Angew. Chem. Int. Ed. Engl. 1985, 24, 976-977.
54. 37. Regitz, M.; J. Hocker, J.; Liedhegener, A. Org. Synth. 1973, Coll. Vol. 5, 179.