Intramolecular C-H insertion reactions of boroxy Fischer carbene complexes. Regio- and diastereoselective modification of terpenes

Journal of the American Chemical Society

Volumn 121, Issue 38, 1999, Pages 8776-8782

  Barluenga, José ^a   Rodríguez, Félix ^a   Vadecard, Jérôme ^a   Bendix, Maximilian ^a   Fañanas, Francisco J ^a   López Ortiz, Fernando ^b   Rodríguez, Miguel A ^c  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF ALMERÍA   (Spain)

^c UNIVERSITY OF LA RIOJA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BORON; TERPENE;

ARTICLE; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; OXIDATION; STEREOCHEMISTRY;

EID: 0043029026     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991161+     Document Type: Article

References (74)

1. (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587.
2. (b) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988.
3. (c) Wulff W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; p 1065.
4. (d) Doyle, M. P. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; p 387.
5. (e) Wulff W. D. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; p 469.
6. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; p 549.
7. Reviews: (a) Erker, G. In Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 143. (b) Erker, G. Polyhedron 1988, 7, 2451. (c) Erker, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
8. Reviews: (a) Erker, G. In Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 143. (b) Erker, G. Polyhedron 1988, 7, 2451. (c) Erker, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
9. Reviews: (a) Erker, G. In Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 143. (b) Erker, G. Polyhedron 1988, 7, 2451. (c) Erker, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
10. (a) Moser, E.; Fischer, E. O. J. Organomet. Chem. 1969, 16, 275.
11. (b) Fischer, E. O.; Selmayr, T.; Kreissl, F. R.; Schubert, U. Chem Ber. 1977, 110, 2574.
12. (c) Fischer, E. O.; Schubert, U.; Kleine, W.; Fischer, H. Inorg. Synth. 1979, 19, 164.
13. (d) Voran, S.; Blau, H.; Malisch, W.; Schubert, U. J. Organomet. Chem. 1982, 232, C33.
14. (e) Balzer, B. L.; Cazanoue, M.; Finn, M. G. J. Am. Chem. Soc. 1992, 114, 8735.
15. (f) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921.
16. (a) Raubenheimer, H. G.; Fischer, E. O. J. Organomet. Chem. 1975, 91, C23.
17. (b) Mashima, K.; Jyodoi, K.; Ohyoshi, A.; Takaya, H. J. Chem. Soc., Chem. Commun. 1986, 1145.
18. (c) Sabat, M.; Gross, M. F.; Finn, M. G. Organometallics 1992, 11, 745.
19. (d) Balzer, B. L.; Cazanoue, M.; Sabat, M.; Finn, M. G. Organometallics 1992, 11, 1759.
20. (e) Beckhaus, R.; Oster, J.; Kempe, R.; Spannenberg, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1565.
21. (a) Wolczanski, P. T.; Threlkel, R. S.; Bercaw, J. E. J. Am. Chem. Soc. 1979, 101, 218.
22. (b) Threlkel, R. S.; Bercaw, J. E. J. Am. Chem. Soc. 1981, 103, 2650.
23. (c) Erker, G.; Dorf, U.; Benn, R.; Reinhardt, R. D. J. Am. Chem. Soc. 1984, 106, 7649.
24. (d) Erker, G.; Dorf, U.; Mynott, R.; Tsay, Y. H.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1985, 24, 584.
25. (e) Beckhaus, R.; Thiele, K. H. J. Organomet. Chem. 1989, 368, 31.
26. (f) Erker, G.; Sosna, F.; Zwettler, R.; Krüger, C. Organometallics 1989, 8, 450.
27. (g) Erker, G.; Sosna, F.; Petersen, J. L.; Benn, R.; Grondey, H. Organometallics 1990, 9, 2462.
28. (h) Erker, G.; Sosna, F.; Betz, P.; Werner, S.; Krüger, C. J. Am. Chem. Soc. 1991, 113, 564.
29. (i) Erker, G.; Berlekamp, M.; López, L.; Grehl, M.; Schönecker, B.; Krieg, R. Synthesis 1994, 212.
30. (a) Erker, G.; Lecht, R. J. Organomet. Chem. 1986, 311, 45.
31. (b) Erker, G.; Lecht, R.; Schlund, K. A.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1987, 26, 666. See also ref 5i.
32. Erker, G.; Mühlenbernd, T.; Benn, R.; Rufinska, A. Organometallics 1986, 5, 402. See also ref 6a.
33. (a) Fischer, E. O.; Gibbins, S. G.; Kellerer, W. J. Organomet. Chem. 1981, 218, C51.
34. (b) Petz, W. Z. Naturforsch. 1981, 36b, 335.
35. a) Barluenga, J.; Canteli, R. M.; Flórez, J.; García-Granda, S.; Gutiérrez-Rodríguez, A. J. Am. Chem. Soc. 1994, 116, 6949.
36. (b) Barluenga J.; Rodríguez, F.; Fañanás, F. J. Organometallics 1997, 16, 5384.
37. (c) Barluenga, J.; Canteli, R. M.; Flórez, J.; García-Granda, S.; Gutiérrez-Rodríguez, A.; Martín, E. J. Am. Chem. Soc. 1998, 120, 2514.
38. (a) Zhao, S. K.; Knors, C.; Helquist, P. J. Am. Chem. Soc. 1989, 111, 8527.
39. (b) Zhao, S. K.; Helquist, P. J. Org. Chem. 1990, 55, 5820.
40. (c) Zhao, S.; Mehta, G.; Helquist, P. Tetrahedron Lett. 1991, 32, 5753.
41. (a) Fischer, H.; Schmid, J.; Maerkl, R. J. Chem. Soc., Chem. Commun. 1985, 572.
42. (b) Fischer, H.; Schmid, J. J. Mol. Catal. 1988, 46, 277.
43. (c) Fischer, H.; Jungklaus, H. J. Organomet. Chem. 1999, 572, 105.
44. Wang, S. L. B.; Su, J.; Wulff, W. D.; Hoogsteen, K. J. Am. Chem. Soc. 1992, 114, 10665.
45. (a) Barluenga, J.; Aznar, F.; Fernández, M. Chem. Eur. J. 1997, 3, 1629.
46. (b) Takeda, K.; Okamoto, Y.; Nakajima, A.; Yoshii, E.; Koizumi, T. Synlett 1997, 1181.
47. Barluenga, J.; Rodríguez, F.; Vadecard, J.; Bendix, M.; Fañanás, F. J.; López-Ortiz, F. J. Am. Chem. Soc. 1996, 118, 6090.
48. (a) Fischer, E. O.; Maasböl, A. Chem Ber. 1967, 100, 2445.
49. Dialkylchloroboranes have been prepared as described in the literature, see: Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767.
50. Diaminochloroboranes have been prepared as described in the literature, see: Aubrey, D. W.; Lappert, M. F.; Majumdar, M. K. J. Chem. Soc. 1962, 4088.
51. According to the suggestion of a reviewer and in order to establish the intramolecular nature of the process, we carried out a crossover experiment with carbene complexes 16e and 21e, which after usual workup resulted in the exclusive formation of diols 18e and 22e.
52. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093.
53. (a) Benn, R.; Brenneke, H.; Heck, J.; Rufinska, A. Inorg. Chem. 1987, 26, 2826.
54. (b) Benn, R.; Rufinska, A.; King, M. A.; Osterberg, C. E.; Richmond, T. J. Organomet. Chem. 1989, 376, 359.
55. (c) Machioni, A.; Pregosin, P. S.; Rüegger, H.; van Koten, G.; van der Schaaf, P. A.; Abbenhuis, R. A. T. M. Magn. Reson. Chem. 1994, 235, 32.
56. 183W δ values of related tungsten complexes, see: (a) Minelli, M.; Enemark, J. H.; Brownlee, T. T. C.; O'Connor, M. J.; Wedd, A. G. Coord. Chem. Rev. 1985, 68, 169. (b) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996 2, 88.
57. 183W δ values of related tungsten complexes, see: (a) Minelli, M.; Enemark, J. H.; Brownlee, T. T. C.; O'Connor, M. J.; Wedd, A. G. Coord. Chem. Rev. 1985, 68, 169. (b) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996 2, 88.
58. 11B NMR spectrum for III because, at the low temperature needed (-50°C), the quadrupolar nature of the boron resulted in an exceedingly large line width.
59. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94 (Revision C.3); Gaussian, Inc.: Pittsburgh, PA, 1995.
60. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
61. Hehre, W. J.; Radom, L.;. Schleyer, P.v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; J. Wiley: New York, 1986.
62. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
63. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
64. Hehre, W. J.: Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
65. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
66. Frenking, G.; Antes, I.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Jonas, V.; Neuhaus, A.; Otto, M.; Stegmann, R.; Veldkamp, A., Vyboishchikov, S. F. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1996; Vol. 8.
67. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
68. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwath, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111.
69. Müller, U. Inorganic Structural Chemistry; Wiley: Chichester, UK, 1993.
70. Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785 and references therein.
71. Brown, H. C.; Malhotra, S. V.; Ramachandran, V. Tetrahedron: Asymmetry 1996, 7, 3527.
72. (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
73. (b) Hodgson, D. M.; Thomson, A. J.; Wadman, S. Tetrahedron Lett. 1998, 39, 3357.
74. (c) Garret, C. E.; Fu, G. C. J. Org. Chem. 1998, 63, 1370.