Catalytic and Structural Studies on Complexes of a Binaphthyl-Phosphino-Oxazoline Auxiliary: The Meta Dialkyl Effect on Enantioselectivity

Organometallics

Volumn 19, Issue 7, 2000, Pages 1299-1307

  Selvakumar, Kumaravel ^a   Valentini, Massimiliano ^a   Pregosin, Paul S ^a   Albinati, Alberto ^b   Eisenträger, Frank ^b  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003298413     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990892f     Document Type: Article

References (80)

1. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; WILEY-VCH: Weinheim, 1998. Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1996. Williams, J. M. J.; Tonks, L. J. Chem. Soc., Perkin Trans. 1 1998, 3637-3652. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: London, 1994. Brown, J. M. Chem. Soc. Rev. 1993, 25. Hayashi, T. Catalytic Asymmetic Synthesis; VCH Publishers: Weinheim, 1993.
2. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; WILEY-VCH: Weinheim, 1998. Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1996. Williams, J. M. J.; Tonks, L. J. Chem. Soc., Perkin Trans. 1 1998, 3637-3652. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: London, 1994. Brown, J. M. Chem. Soc. Rev. 1993, 25. Hayashi, T. Catalytic Asymmetic Synthesis; VCH Publishers: Weinheim, 1993.
3. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; WILEY-VCH: Weinheim, 1998. Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1996. Williams, J. M. J.; Tonks, L. J. Chem. Soc., Perkin Trans. 1 1998, 3637-3652. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: London, 1994. Brown, J. M. Chem. Soc. Rev. 1993, 25. Hayashi, T. Catalytic Asymmetic Synthesis; VCH Publishers: Weinheim, 1993.
4. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; WILEY-VCH: Weinheim, 1998. Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1996. Williams, J. M. J.; Tonks, L. J. Chem. Soc., Perkin Trans. 1 1998, 3637-3652. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: London, 1994. Brown, J. M. Chem. Soc. Rev. 1993, 25. Hayashi, T. Catalytic Asymmetic Synthesis; VCH Publishers: Weinheim, 1993.
5. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; WILEY-VCH: Weinheim, 1998. Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1996. Williams, J. M. J.; Tonks, L. J. Chem. Soc., Perkin Trans. 1 1998, 3637-3652. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: London, 1994. Brown, J. M. Chem. Soc. Rev. 1993, 25. Hayashi, T. Catalytic Asymmetic Synthesis; VCH Publishers: Weinheim, 1993.
6. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; WILEY-VCH: Weinheim, 1998. Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1996. Williams, J. M. J.; Tonks, L. J. Chem. Soc., Perkin Trans. 1 1998, 3637-3652. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: London, 1994. Brown, J. M. Chem. Soc. Rev. 1993, 25. Hayashi, T. Catalytic Asymmetic Synthesis; VCH Publishers: Weinheim, 1993.
7. (a) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395, and references therein.
8. (b) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gange, M. R. J. Org. Chem. 1999, 64, 2994-2995.
9. (c) Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581-5582.
10. (d) Tamaru, Y. J. Organomet. Chem. 1999, 576, 215-231.
11. (e) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540.
12. (f) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681-1687.
13. (g) Bower, J. F.; Williams, J. M. J. Synlett 1996, 685.
14. (h) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506.
15. (i) Reiser, O. Angew. Chem. 1993, 105, 576.
16. (j) Hayashi, T.; Yamamoto, A.; Ito, Y. N., E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301.
17. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 4. Amatore, C.; Jutland, A. J. Organomet. Chem. 1999, 576, 254-278. Overman, L. E.; Link, J. T. In Intramolecular Heck Reactions in Natural Product Chemistry; Overman, L. E., Link, J. T., Eds.; Wiley- VCH: Weinheim, 1998; pp 239-266. Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C. P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257-259. Pfaltz, A. Acta Chem. Scand. 1996, 50, 189-194. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506.
18. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 4. Amatore, C.; Jutland, A. J. Organomet. Chem. 1999, 576, 254-278. Overman, L. E.; Link, J. T. In Intramolecular Heck Reactions in Natural Product Chemistry; Overman, L. E., Link, J. T., Eds.; Wiley- VCH: Weinheim, 1998; pp 239-266. Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C. P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257-259. Pfaltz, A. Acta Chem. Scand. 1996, 50, 189-194. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506.
19. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 4. Amatore, C.; Jutland, A. J. Organomet. Chem. 1999, 576, 254-278. Overman, L. E.; Link, J. T. In Intramolecular Heck Reactions in Natural Product Chemistry; Overman, L. E., Link, J. T., Eds.; Wiley- VCH: Weinheim, 1998; pp 239-266. Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C. P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257-259. Pfaltz, A. Acta Chem. Scand. 1996, 50, 189-194. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506.
20. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 4. Amatore, C.; Jutland, A. J. Organomet. Chem. 1999, 576, 254-278. Overman, L. E.; Link, J. T. In Intramolecular Heck Reactions in Natural Product Chemistry; Overman, L. E., Link, J. T., Eds.; Wiley-VCH: Weinheim, 1998; pp 239-266. Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C. P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257-259. Pfaltz, A. Acta Chem. Scand. 1996, 50, 189-194. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506.
21. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 4. Amatore, C.; Jutland, A. J. Organomet. Chem. 1999, 576, 254-278. Overman, L. E.; Link, J. T. In Intramolecular Heck Reactions in Natural Product Chemistry; Overman, L. E., Link, J. T., Eds.; Wiley- VCH: Weinheim, 1998; pp 239-266. Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C. P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257-259. Pfaltz, A. Acta Chem. Scand. 1996, 50, 189-194. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506.
22. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 4. Amatore, C.; Jutland, A. J. Organomet. Chem. 1999, 576, 254-278. Overman, L. E.; Link, J. T. In Intramolecular Heck Reactions in Natural Product Chemistry; Overman, L. E., Link, J. T., Eds.; Wiley- VCH: Weinheim, 1998; pp 239-266. Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C. P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257-259. Pfaltz, A. Acta Chem. Scand. 1996, 50, 189-194. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506.
23. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 4. Amatore, C.; Jutland, A. J. Organomet. Chem. 1999, 576, 254-278. Overman, L. E.; Link, J. T. In Intramolecular Heck Reactions in Natural Product Chemistry; Overman, L. E., Link, J. T., Eds.; Wiley- VCH: Weinheim, 1998; pp 239-266. Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C. P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257-259. Pfaltz, A. Acta Chem. Scand. 1996, 50, 189-194. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506.
24. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Noyori, R. Chimia 1988, 42, 215. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345. Takaya, H.; Ohta, T.; Mashina, K.; Noyori, R. Pure Appl. Chem. 1990, 62, 1135-1138. Takaya, H.; Ohta, T.; Mashima, K. In Homogeneous Transition Metal Catalysed Reactions; Moser, W. R., Slocum, D. W., Eds.; American Chemical Society: Washington DC, 1992; Vol. 230.
25. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Noyori, R. Chimia 1988, 42, 215. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345. Takaya, H.; Ohta, T.; Mashina, K.; Noyori, R. Pure Appl. Chem. 1990, 62, 1135-1138. Takaya, H.; Ohta, T.; Mashima, K. In Homogeneous Transition Metal Catalysed Reactions; Moser, W. R., Slocum, D. W., Eds.; American Chemical Society: Washington DC, 1992; Vol. 230.
26. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Noyori, R. Chimia 1988, 42, 215. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345. Takaya, H.; Ohta, T.; Mashina, K.; Noyori, R. Pure Appl. Chem. 1990, 62, 1135-1138. Takaya, H.; Ohta, T.; Mashima, K. In Homogeneous Transition Metal Catalysed Reactions; Moser, W. R., Slocum, D. W., Eds.; American Chemical Society: Washington DC, 1992; Vol. 230.
27. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Noyori, R. Chimia 1988, 42, 215. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345. Takaya, H.; Ohta, T.; Mashina, K.; Noyori, R. Pure Appl. Chem. 1990, 62, 1135-1138. Takaya, H.; Ohta, T.; Mashima, K. In Homogeneous Transition Metal Catalysed Reactions; Moser, W. R., Slocum, D. W., Eds.; American Chemical Society: Washington DC, 1992; Vol. 230.
28. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102. Noyori, R. Chimia 1988, 42, 215. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345. Takaya, H.; Ohta, T.; Mashina, K.; Noyori, R. Pure Appl. Chem. 1990, 62, 1135-1138. Takaya, H.; Ohta, T.; Mashima, K. In Homogeneous Transition Metal Catalysed Reactions; Moser, W. R., Slocum, D. W., Eds.; American Chemical Society: Washington DC, 1992; Vol. 230.
29. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde M.; Mueller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131.
30. Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron Asymmetry 1991, 2, 569-592. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
31. Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron Asymmetry 1991, 2, 569-592. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
32. (a) von Matt, Loiseleur, O.; Koch, G.; Pfaltz, A.; Lefeber, C.; Feucht, T. Helmchen, G. Tetrahedron Asymmetry 1994, 5, 573.
33. (b) Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381-1384.
34. (c) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron Asymmetry 1996, 7, 1599-1602.
35. (d) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047-3050.
36. Schnyder, A.; Togni, A.; Wiesli, U. Organometallics 1997, 16, 255-260.
37. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343-4346.
38. Selvakumar, K.; Valentini, M.; Wörle, M.; Pregosin, P. S.; Albinati, A. Organometallics 1999, 18, 1207-1215.
39. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315.
40. Tschoerner, M.; Pregosin, P. S.; Albinati, A. Organometallics 1999, 18, 670-678.
41. Hayashi and co-workers report the same ee using the same P,N ligand; see: Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron Asymmetry 1998, 9, 1779-1787.
42. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188- 4196.
43. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188-4196.
44. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16-22.
45. Pfaltz, A.; Prétôt, R. Angew. Chem. 1998, 110, 337-339. Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem. 1996, 108, 218.
46. Pfaltz, A.; Prétôt, R. Angew. Chem. 1998, 110, 337-339. Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem. 1996, 108, 218.
47. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1-S83.
48. Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5150.
49. Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Köllner, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1995, 14, 759-766.
50. Since one P-aryl ring rotates freely, despite the stacking interaction, its ortho protons come close enough to the proximate naphthyl moiety to afford modest NOEs
51. From a steric point of view, an olefin aryl complex would be a much better model.
52. Pregosin, P. S.; Trabesinger, G. J. Chem. Soc., Dalton Trans. 1998, 727-734. Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35-68.
53. Pregosin, P. S.; Trabesinger, G. J. Chem. Soc., Dalton Trans. 1998, 727-734. Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35-68.
54. Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. Helmchen, G.; Reggelein, M.; Huttner, G.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-1526. Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
55. Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. Helmchen, G.; Reggelein, M.; Huttner, G.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-1526. Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
56. Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. Helmchen, G.; Reggelein, M.; Huttner, G.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-1526. Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
57. Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
58. Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5150. Barbara, P.; Currao, A.; Herrmann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics, 1996, 15, 1879-1888. Albinati, A.; Eckert, J.; Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579- 590. Boog-Wick, K.; Pregosin, P. S.; Trabesinger, G. Organometallics 1998, 17, 3254-3264.
59. Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5150. Barbara, P.; Currao, A.; Herrmann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics, 1996, 15, 1879-1888. Albinati, A.; Eckert, J.; Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579- 590. Boog-Wick, K.; Pregosin, P. S.; Trabesinger, G. Organometallics 1998, 17, 3254-3264.
60. Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5150. Barbara, P.; Currao, A.; Herrmann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics, 1996, 15, 1879-1888. Albinati, A.; Eckert, J.; Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. Boog-Wick, K.; Pregosin, P. S.; Trabesinger, G. Organometallics 1998, 17, 3254-3264.
61. Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5150. Barbara, P.; Currao, A.; Herrmann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics, 1996, 15, 1879-1888. Albinati, A.; Eckert, J.; Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579- 590. Boog-Wick, K.; Pregosin, P. S.; Trabesinger, G. Organometallics 1998, 17, 3254-3264.
62. Valentini, M.; Selvakumar, K.; Worle, M.; Pregosin, P. S. J. Organomet. Chem. 1999, 587, 244-251.
63. Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; Rajanbabu, T. V. J. Org. Chem. 1999, 64, 7601-7611.
64. Rajanbabu, T. V.; Ayers, T. A.; Caasalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.
65. Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem. 1999, 111, 517-519.
66. Blaser, H. U.; Buser, H. P.; Jalet, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867-868.
67. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.
68. Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503.
69. 34 have suggested that the olefin insertion is rapid.
70. Brown, J. M.; Perez-Torrente, J.; Alcock, N.; Clase, H. J. Organometallics 1995, 14, 207. Brown, J. M.; Hii, K. K. Angew. Chem. 1996, 108, 679. Hii, K. K.; Claridge, T. D. W.; Brown, J. M. Angew. Chem. 1997, 109, 1033-1036. Deeth, R. J.; Smith, A.; Hu, K. K.; Brown, J. M. Tetrahedron Lett. 1998, 39, 3229-3232.
71. Brown, J. M.; Perez-Torrente, J.; Alcock, N.; Clase, H. J. Organometallics 1995, 14, 207. Brown, J. M.; Hii, K. K. Angew. Chem. 1996, 108, 679. Hii, K. K.; Claridge, T. D. W.; Brown, J. M. Angew. Chem. 1997, 109, 1033-1036. Deeth, R. J.; Smith, A.; Hu, K. K.; Brown, J. M. Tetrahedron Lett. 1998, 39, 3229-3232.
72. Brown, J. M.; Perez-Torrente, J.; Alcock, N.; Clase, H. J. Organometallics 1995, 14, 207. Brown, J. M.; Hii, K. K. Angew. Chem. 1996, 108, 679. Hii, K. K.; Claridge, T. D. W.; Brown, J. M. Angew. Chem. 1997, 109, 1033-1036. Deeth, R. J.; Smith, A.; Hu, K. K.; Brown, J. M. Tetrahedron Lett. 1998, 39, 3229-3232.
73. Brown, J. M.; Perez-Torrente, J.; Alcock, N.; Clase, H. J. Organometallics 1995, 14, 207. Brown, J. M.; Hii, K. K. Angew. Chem. 1996, 108, 679. Hii, K. K.; Claridge, T. D. W.; Brown, J. M. Angew. Chem. 1997, 109, 1033-1036. Deeth, R. J.; Smith, A.; Hu, K. K.; Brown, J. M. Tetrahedron Lett. 1998, 39, 3229-3232.
74. de Graaf, W.; Boersma, J.; van Koten, G.; Elsevier: C. J. J. Organomet. Chem. 1989, 378, 115-124. Tschoerner. M.; Kunz, R. W.; Pregosin, P. S. Magn. Reson. Chem. 1999, 37, 91-97.
75. de Graaf, W.; Boersma, J.; van Koten, G.; Elsevier: C. J. J. Organomet. Chem. 1989, 378, 115-124. Tschoerner. M.; Kunz, R. W.; Pregosin, P. S. Magn. Reson. Chem. 1999, 37, 91-97.
76. SAINT: Area Detector Integration; Siemens Analytical Instrumentation, 1996.
77. Sheldrick, G. M. SADABS; Universität Göttingen. To be published.
78. Sheldrick, G. M SHELX-97. Structure Solution and Refinement Package; Universität Göttingen, 1997.
79. Flack, H. D. Acta Crystallogr. 1983, A39, 876.
80. International Tables for X-ray Crystallography; Wilson A. J. C., Ed.; Kluwer Academic Publisher: Dordrecht, The Netherlands, 1992; Vol. C, Tables 6.1.1.4, 4.2.6.8, 4.2.4.2.