Role of electronic asymmetry in the design of new ligands: The asymmetric hydrocyanation reaction

Journal of the American Chemical Society

Volumn 118, Issue 26, 1996, Pages 6325-6326

  RajanBabu, T V ^b   Casalnuovo, Albert L ^a  

^a DUPONT COMPANY   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE;

ARTICLE; CHIRALITY; DRUG DESIGN; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030040083     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9609112     Document Type: Article

References (50)

1. (a) Kagan, H. B. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985: Vol. 5, pp 1-39.
2. (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
3. (c) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
4. (d) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
5. (e) Otsuka, S.; Tani, K. Synthesis 1991, 665.
6. (a) Kagan, H. B. in Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W. Ed.; Pergamon Press: Oxford, 1982; Vol. 8, p 463.
7. (b) Noyori, R. Asymmetric Catalysis: John Wiley: New York, 1994.
8. (c) Ojima, I. Asymmetric Synthesis', Verlag: New York, 199(3) Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O. J. Am. Chem. Soc. 1976, 98, 6188.
9. (c) Ojima, I. Asymmetric Synthesis', Verlag: New York, 199(3) Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O. J. Am. Chem. Soc. 1976, 98, 6188.
10. Whitesell, J. K. Acc. Chem. Res. 1985, 18, 280.
11. (a) Pavlov, V. A.; Klabunovskii, E. I.; Struchkov, Y. T.; Voloboev, A. A.; Yanovski, A. I. J. Mol. Catal. 1988, 44, 217.
12. (b) Brown, J. M.; Evans, P. L. Tetrahedron 1988, 44, 4905.
13. (c) Nagel, U.; Rieger, B. Organometallics 1989, 8, 1534.
14. (d) Bogdan, P. L.; Irwin, J. J.; Bosnich, B. Organometallics 1989, 8, 1450.
15. (e) Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Petter, W. Helv. Chim. Acta 1992, 75, 2171.
16. (f) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
17. For some recent examples, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and references cited therein, (b) Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997.
18. For some recent examples, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and references cited therein, (b) Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997.
19. For some recent examples, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 and references cited therein, (b) Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997.
20. For a review of the pioneering contributions of the Achiwa group, see: Inoguchi, K.; Sakuraba. S.; Achiwa, K. Synlett 1992, 169.
21. Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703.
22. Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306.
23. (a) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265.
24. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.
25. (c) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. J. Am. Chem. Soc. 1994, 116, 9869.
26. (d) RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295.
27. Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931.
28. For reviews: Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; Reiser, O. Angew. Chem., Int. Ed Engl. 1993, 32, 547.
29. For reviews: Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089; Reiser, O. Angew. Chem., Int. Ed Engl. 1993, 32, 547.
30. For representative examples from various research groups see the following references and others cited therein: (a) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (b) Rieck, H.; Helmchen, G. Angew, Chem., Int. Ed. Engl. 1995, 34, 2687. (c) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (d) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1994, 115, 7033. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; p 325.
31. For representative examples from various research groups see the following references and others cited therein: (a) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (b) Rieck, H.; Helmchen, G. Angew, Chem., Int. Ed. Engl. 1995, 34, 2687. (c) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (d) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1994, 115, 7033. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; p 325.
32. For representative examples from various research groups see the following references and others cited therein: (a) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (b) Rieck, H.; Helmchen, G. Angew, Chem., Int. Ed. Engl. 1995, 34, 2687. (c) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (d) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1994, 115, 7033. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; p 325.
33. For representative examples from various research groups see the following references and others cited therein: (a) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (b) Rieck, H.; Helmchen, G. Angew, Chem., Int. Ed. Engl. 1995, 34, 2687. (c) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (d) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1994, 115, 7033. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; p 325.
34. For representative examples from various research groups see the following references and others cited therein: (a) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. (b) Rieck, H.; Helmchen, G. Angew, Chem., Int. Ed. Engl. 1995, 34, 2687. (c) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (d) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1994, 115, 7033. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; p 325.
35. For a lucid discussion, see: Bosnich, B. Asymmetric Catalysis; Martinus Ninjhoff Publishers: Dordrecht, The Netherlands, 1986.
36. For a relevant example in the oxidative addition of HT to Ir(I), see: Crabtree, R. H.; Uriarte, R. J. Inorg. Chem. 1983, 22, 4152.
37. 18 of hydrogen and the attendant enantioselectivity.
38. Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746.
39. Bender, B. R.; Koller, M.; Nanz, D.; von Philipsborn, W. J. Am. Chem. Soc. 1993, 115, 5889.
40. 8-metals, see: Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 3148. Sargent, A. L.; Hall, M. B.; Guest, M. F. J. Am. Chem. Soc. 1992, 114, 517.
41. 8-metals, see: Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 3148. Sargent, A. L.; Hall, M. B.; Guest, M. F. J. Am. Chem. Soc. 1992, 114, 517.
42. (a) Yamagishi, T.; Yatagai, M.; Hatakeyama, H.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 1897.
43. (b) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1988, 29, 4755.
44. (c) Werz, U.; Brune, H. J. Organomet. Chem. 1989, 365, 367.
45. (d) Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull 1992, 40, 2894.
46. For a solution to this problem in the context of the Rh-catalyzed hydrogenation route to amino acids see ref 10b.
47. Bourson, J.; Laureano, O. J. Organomet. Chem. 1982, 229, 77.
48. For electronic effects on reductive elimination, see: Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181.
49. For a review of trans effects, see: Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335. For a recent example, see: van Leeuwen, P. W. N. M.; Roobeek, C. F.; van der Heijden, H. J. Am. Chem. Soc. 1994, 116, 12117.
50. For a review of trans effects, see: Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335. For a recent example, see: van Leeuwen, P. W. N. M.; Roobeek, C. F.; van der Heijden, H. J. Am. Chem. Soc. 1994, 116, 12117.