Stereochemical probes of intramolecular C-H insertion reactions of iron- carbene complexes [11]

Journal of the American Chemical Society

Volumn 122, Issue 24, 2000, Pages 5897-5898

  Ishii, Shingo ^a   Zhao, Shikai ^a   Helquist, Paul ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE;

ALKYLATION; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; LETTER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034697674     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000239f     Document Type: Letter

References (61)

1. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
2. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
3. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
4. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
5. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
6. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
7. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
8. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
9. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
10. For reviews of carbenes, carbene complexes, and insertion reactions, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919. (b) Maas, G. Top. Curr. Chem. 1987, 137, 75. (c) Taber, D. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pattenden, G., Vol. Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1045-1062. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765-1808. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453. (f) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160. (g) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 421-468. (h) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: from Cyclopropanes to Ylides; Wiley: New York, 1998. (i) Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2. (j) Sulikowski, G, A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145-3169.
11. (a) Zhao, S.-K.; Knors, C.; Helquist, P. J. Am. Chem. Soc. 1989, 111, 8527-8528.
12. (b) Ishii, S.; Helquist, P. Synlett 1997, 508-510.
13. For reviews of iron-carbene complexes, see: (a) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (b) Helquist, P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, pp 143-194. (c) Fatiadi, A. J. J. Res. Natl. Inst. Stand. Technol. 1991, 96, 1-113. (d) Petz, W. Iron-Carbene Complexes; Springer-Verlag: Berlin, 1993. (e) Guerchais, V. Bull. Soc. Chim. Fr. 1994, 131, 803-811. (f) Ruck- Braun, K.; Mikulas, M.; Amrhein, P. Synthesis 1999, 727-744.
14. For reviews of iron-carbene complexes, see: (a) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (b) Helquist, P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, pp 143-194. (c) Fatiadi, A. J. J. Res. Natl. Inst. Stand. Technol. 1991, 96, 1-113. (d) Petz, W. Iron-Carbene Complexes; Springer-Verlag: Berlin, 1993. (e) Guerchais, V. Bull. Soc. Chim. Fr. 1994, 131, 803-811. (f) Ruck- Braun, K.; Mikulas, M.; Amrhein, P. Synthesis 1999, 727-744.
15. For reviews of iron-carbene complexes, see: (a) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (b) Helquist, P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, pp 143-194. (c) Fatiadi, A. J. J. Res. Natl. Inst. Stand. Technol. 1991, 96, 1-113. (d) Petz, W. Iron-Carbene Complexes; Springer-Verlag: Berlin, 1993. (e) Guerchais, V. Bull. Soc. Chim. Fr. 1994, 131, 803-811. (f) Ruck- Braun, K.; Mikulas, M.; Amrhein, P. Synthesis 1999, 727-744.
16. For reviews of iron-carbene complexes, see: (a) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (b) Helquist, P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, pp 143-194. (c) Fatiadi, A. J. J. Res. Natl. Inst. Stand. Technol. 1991, 96, 1-113. (d) Petz, W. Iron-Carbene Complexes; Springer-Verlag: Berlin, 1993. (e) Guerchais, V. Bull. Soc. Chim. Fr. 1994, 131, 803-811. (f) Ruck- Braun, K.; Mikulas, M.; Amrhein, P. Synthesis 1999, 727-744.
17. For reviews of iron-carbene complexes, see: (a) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (b) Helquist, P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, pp 143-194. (c) Fatiadi, A. J. J. Res. Natl. Inst. Stand. Technol. 1991, 96, 1-113. (d) Petz, W. Iron-Carbene Complexes; Springer-Verlag: Berlin, 1993. (e) Guerchais, V. Bull. Soc. Chim. Fr. 1994, 131, 803-811. (f) Ruck- Braun, K.; Mikulas, M.; Amrhein, P. Synthesis 1999, 727-744.
18. For reviews of iron-carbene complexes, see: (a) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. (b) Helquist, P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, pp 143-194. (c) Fatiadi, A. J. J. Res. Natl. Inst. Stand. Technol. 1991, 96, 1-113. (d) Petz, W. Iron-Carbene Complexes; Springer-Verlag: Berlin, 1993. (e) Guerchais, V. Bull. Soc. Chim. Fr. 1994, 131, 803-811. (f) Ruck-Braun, K.; Mikulas, M.; Amrhein, P. Synthesis 1999, 727-744.
19. (a) Zhao, S.-K.; Helquist, P. J. Org. Chem. 1990, 55, 5820-5821.
20. (b) Zhao, S.; Mehta, G.; Helquist, P. Tetrahedron Lett. 1991, 32, 5753-5756.
21. (a) Guerchais, V.; Sinbandhit, S. J. Chem. Soc., Chem. Commun. 1990, 1550-1552.
22. (b) Scharrer, E.; Brookhart, M. J. Organomet. Chem. 1995, 497, 61-71.
23. (a) Knors, C.; Kuo, G.-H.; Lauher, J. W.; Eigenbrot, C.; Helquist, P. Organometallics 1987, 6, 988-995.
24. (b) Knors, C.; Helquist, P. Organomet. Synth. 1988, 4, 205-209.
25. Meerwein, H. Organic Syntheses; Baumgarten, H. E., Ed.; Wiley: New York, 1973; Collect. Vol. V, pp 1096-1103.
26. 13C NMR spectra of these compounds and their separately prepared, non-deuterated counterparts.
27. Stereoselective syntheses of these substrates are described in the Supporting Information.
28. This experiment was performed four times to give a product ratio of 2.7 ± 0.3.
29. (a) Ring, D. F.; Rabinovitch, B. S. Can. J. Chem. 1968, 46, 2435-2450.
30. (b) Baer, T. A.; Gutsche, C. D. J. Am. Chem. Soc. 1971, 93, 5180-5186.
31. (c) Barcus, R. L.; Hadel, L. M.; Johnston, L. J.; Platz, M. S.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1986, 108, 3928-3937.
32. (d) Savino, T. G.; Kanakarajan, K.; Platz, M. S. J. Org. Chem. 1986, 51, 1305-1309.
33. (e) Oku, A.; Harada, T.; Hattori, K.; Nozaki, Y.; Yamaura, Y. J. Org. Chem. 1988, 53, 3089-3098.
34. (f) Pascal, R. A., Jr.; Mischke, S. J. Org. Chem. 1991, 50, 6954-6957.
35. (g) Kirmse, W.; Özkir, I. S.; Schnitzler, D. J. Am. Chem. Soc. 1993, 115, 792-793.
36. (h) Miebach, T.; Wüster, H.; Brinker, U. H. J. Org. Chem. 1993, 58, 6520-6523.
37. (i) Moss, R. A.; Liu, W. Tetrahedron Lett. 1996, 37, 279-282.
38. (j) Moss, R. A.; Yan, S. Tetrahedron Lett. 1998, 39, 9381-9384.
39. (k) Moss, R. A.; Yan, S. Org. Lett. 1999, 1, 819-822.
40. (a) Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686-7693.
41. (b) Fischer, H.; Schmid, J. J. Mol. Catal. 1988, 46, 277-285.
42. (c) Demonceau, A.; Noels, A. F.; Costa, J.-L.; Hubert, A. J. J. Mol. Catal. 1990, 58, 21-26.
43. (d) Wang, S. L. B.; Su, J.; Wulff, W. D.; Hoogsteen, K. J. Am. Chem. Soc. 1992, 114, 10665-10666.
44. (e) Spero, D. M.; Adams, J. Tetrahedron Lett. 1992, 33, 1143-1146.
45. (f) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958-964.
46. (g) Aumann, R.; Läge, M.; Krebs, B. Chem. Ber. 1994, 127, 731-738.
47. (h) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296-3305.
48. (i) Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1994, 116, 8991-9000.
49. (j) Doyle, M. P.; Dyatkin, A. B.; Autry, C. I. J. Chem. Soc., Perkin Trans. 1 1995, 619-621.
50. (k) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547-556.
51. (l) Barluenga, J.; Rodríguez, F.; Vadecard, J.; Bendix, M.; Fañanás, F. J.; López-Ortiz, F. J. Am. Chem. Soc. 1996, 118, 6090-6091.
52. (m) Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 6706-6712.
53. (n) Barluenga, J.; Aznar, F.; Fernandez, M. Chem. Eur. J. 1997, 3, 1629-1637.
54. (o) Clark, J. S.; Dossetter, A. G.; Russell, C. A.; Whittingham, W. G. J. Org. Chem. 1997, 62, 4910-4911.
55. (p) Takeda, K.; Okamoto, Y.; Nakajima, A.; Yoshii, E.; Koizumi, T. Synlett 1997 1181.
56. (q) Wang, J.; Chen, B.; Bao, J. J. Org. Chem. 1998, 63, 1853-1862.
57. (r) Wang, J.; Liang, F.; Chen, B. J. Org. Chem. 1998, 63, 8589-8594.
58. (s) Barluenga, J.; Rodríguez, F.; Vadecard, J.; Bendix, M.; Fañanás, F. J.; Lépez-Ortiz, F.; Rodríguez, M. A. J. Am. Chem. Soc. 1999, 121, 8776-8782.
59. (t) White, J. D.; Hrnciar, P. J. Org. Chem. 1999, 64, 7271-7273.
60. (u) Sulikowski, G. A.; Lee, S. Tetrahedron Lett. 1999, 40, 8035-8038.
61. Brookhart, M.; Kegley, S. E.; Husk, G. R. Organometallics 1984, 3, 650-652.