Synthesis of planar chiral (1,2-disubstituted arene)chromium tricarbonyl compounds and their application in asymmetric hydroboration

Organometallics

Volumn 17, Issue 15, 1998, Pages 3236-3239

  Son, Seung Uk ^a   Jang, Hye Young ^a   Lee, In Su ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001481299     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980228j     Document Type: Article

References (51)

1. (a) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. Ed.; JAI: Greenwich, CT, 1989; Vol. 1, pp 99-133.
2. (b) Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. Ed.; JAI: Greenwich, CT, 1991; Vol. 2, pp 199-245.
3. (c) Kündig, E. P.; Bernardinelli, G.; Liu, R.; Ripa, A. J. Am. Chem. Soc. 1991, 113, 9676.
4. (d) Mukai, C.; Miyakawa, M.; Mihira, A.; Hanaoka, M. J. Org. Chem. 1992, 57, 2034.
5. (e) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M. Hayashi, Y. J. Org. Chem. 1993, 58, 1238.
6. (f) Kündig, E. P.; Xu, L. H.; Romanens, P.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 7049.
7. (g) Davies, S. G.; Hume, W. E. J. Chem. Soc., Chem. Commun. 1995, 251.
8. (h) Davies, S. G.; Correia, M. A. R. B. J. Chem. Soc., Chem. Commun. 1996, 1803.
9. (i) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375.
10. (j) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088.
11. (k) Schmalz, H.; Siegel, S.; Schwarz, A. Tetrahedron Lett. 1996, 37, 2947.
12. (l) Semmelhack, M. F.; Schmalz, H. Tetrahedron Lett. 1996, 37, 3089.
13. (m) Pearson, A. J.; Gontchartov, A. V.; Woodgate, P. D. Tetrahedron Lett. 1996, 37, 3087.
14. (n) Quattropani, A.; Anderson, G.; Bernardinelli, G.; Kündig, E. P. J. Am. Chem. Soc. 1997, 119, 4773.
15. (a) Baldoli, C.; Del Buttero, P. J. Chem. Soc., Chem. Commun. 1991, 982.
16. (b) Heaton, S. B.; Jones, G. B. Tetrahedron Lett. 1992, 33, 1693.
17. (c) Uemura, M.; Hayashi, Y.; Hayashi, Y. Tetrahedron: Asymmetry 1993, 4, 2291.
18. (d) Jones, G. B.; Heaton, S. B. Tetrahedron: Asymmetry 1993, 4, 261.
19. (e) Jones, G. B.; Chapman, B. J.; Huber, R. S.; Beaty, R. Tetrahedron: Asymmetry 1994, 5, 1199.
20. (f) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475.
21. (g) Jones, G. B.; Huber, R. S.; Chapman, B. J. Tetrahedron: Asymmetry 1997, 8, 1797.
22. (h) Jones, G. B.; Heaton, S. B.; Chapman, B. J.; Guzel, M. Tetrahedron: Asymmetry 1997, 8, 3625.
23. (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199.
24. (b) Alexakis, A.; Mangeney, P.; Marek, I.; Rose-Munch, F.; Rose, E.; Semra, A.; Robert, F. J. Am. Chem. Soc. 1992, 114, 8288.
25. (c) Aubé, J.; Heppert, J. A.; Miligan, M. L.; Smith, M. J.; Zenk, P. J. Org. Chem. 1992, 57, 3563.
26. (d) Price, D. A.; Simpkins, N. S.; MacLeod, A. M.; Watt, A. P. J. Org. Chem. 1994, 59, 1961.
27. (e) Schmalz, H.; Schellhaas, K. Tetrahedron Lett. 1995, 36, 5515.
28. (f) Amurrio, D.; Khan, K.; Kündig, E. P. J. Org. Chem. 1996, 61, 2258.
29. (g) Siwek, M. J.; Green, J. R. J. Chem. Soc., Chem. Commun. 1996, 2359.
30. (h) Ewin, R. A.; MacLeod, A. M.; Price, D. A.; Simpkins, N. S.; Watt, A. P. J. Chem. Soc., Perkin Trans 1 1997, 401.
31. Han, J. W.; Son, S. U.; Chung, Y. K. J. Org. Chem. 1997, 62, 8264.
32. (a) Brown, J. M.; Hulmes, D. I.; Laysell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673.
33. (b) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931.
34. (c) Schnyder, A.; Togni, A.; Wiesli, U. Organometallics 1997, 16, 255.
35. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
36. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
37. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
38. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
39. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
40. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
41. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
42. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
43. Rh complexes: (a) Männig, D.; Nöth, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 878. Zr complexes: (b) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127. (c) Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909. Ir complexes: (d) Evans, D. A.; Fu, G. U.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Ni complexes: (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. Ru complexes: (f) Burgess, K.; Jaspars, M. Organometallics 1993, 12, 4197. Pd complexes: (g) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732. (h) Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1993, 1468. Ln complexes: (i) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
44. (a) Evans, D. A.; Fu, C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917.
45. (b) Evans, D. A.; Fu, C.; Anderson, B. A. J. Am. Chem. Soc. 1992, 114, 6679.
46. (c) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350.
47. (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863.
48. (b) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: New York, 1988.
49. (a) Burgess, K.; van der Donk, W. A.; Kook, A. M. J. Org. Chem. 1991, 56, 2949.
50. (b) Zhang, J.; Lou, B.; Guo, G.; Dai, L. J. Org. Chem. 1991, 56, 1670.
51. Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426.