Nucleophilic catalysis with π-bound nitrogen heterocycles: Synthesis of the first ruthenium catalysts and comparison of the reactivity and the enantioselectivity of ruthenium and iron complexes

Journal of the American Chemical Society

Volumn 120, Issue 30, 1998, Pages 7479-7483

  Garrett, Christine E ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; MOLECULAR DYNAMICS; REACTION ANALYSIS;

EID: 0032486788     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981061o     Document Type: Article

References (43)

1. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt. N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
2. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
3. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
4. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
5. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
6. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
7. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
8. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
9. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
10. For example, see: (a) Acylation of alcohols: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169-3170. (b) Aldol: Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405. (c) Allylation of aldehydes: Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (d) Reduction of ketones: Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178. (e) [2+2] Cycloaddition: Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. (f) [3+2] Cycloaddition: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
11. Kinetic resolution of secondary alcohols: (a) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230-7231. (b) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492-1493. (c) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794-2795.
12. Kinetic resolution of secondary alcohols: (a) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230-7231. (b) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492-1493. (c) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794-2795.
13. Kinetic resolution of secondary alcohols: (a) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230-7231. (b) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492-1493. (c) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794-2795.
14. Dynamic kinetic resolution of azlactones: Liang, J.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1998, 63, 3154-3155.
15. (a) Scriven, E. F. V. Chem. Soc. Rev. 1983, 12, 129-161.
16. (b) Hassner, A.; Krepski, L. R.; Alexanian, V. Tetrahedron 1978, 34, 2069-2076.
17. (c) Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569-583.
18. Reference 2c and unpublished results (J. C. Ruble).
19. For studies comparing ferrocene-and ruthenocene-derived ligands, sec: (a) Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221-4226. (b) Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Martelletti, A.; Spencer, J.; Steiner, I.; Togni, A. Organometallics 1996, 15, 1614-1621. (c) Li, S.; Wei, B.; Low, P. M. N.; Lee, H. K.; Hor, T. S. A.; Xue, F.; Mak, T. C. W. J. Chem. Soc., Dalton Trans. 1997, 1289-1293.
20. For studies comparing ferrocene-and ruthenocene-derived ligands, sec: (a) Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221-4226. (b) Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Martelletti, A.; Spencer, J.; Steiner, I.; Togni, A. Organometallics 1996, 15, 1614-1621. (c) Li, S.; Wei, B.; Low, P. M. N.; Lee, H. K.; Hor, T. S. A.; Xue, F.; Mak, T. C. W. J. Chem. Soc., Dalton Trans. 1997, 1289-1293.
21. For studies comparing ferrocene-and ruthenocene-derived ligands, sec: (a) Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221-4226. (b) Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Martelletti, A.; Spencer, J.; Steiner, I.; Togni, A. Organometallics 1996, 15, 1614-1621. (c) Li, S.; Wei, B.; Low, P. M. N.; Lee, H. K.; Hor, T. S. A.; Xue, F.; Mak, T. C. W. J. Chem. Soc., Dalton Trans. 1997, 1289-1293.
22. (a) Turbitt, T. D.; Watts, W. E. J. Chem. Soc., Perkin Trans. 2 1974, 185-189.
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26. Slocum, D. W.; Duraj, S.; Matusz, M.; Cmarik, J. L.; Simpson, K. M.; Owen, D. A. In Metal-Containing Polymeric Systems; Plenum: New York, 1985.
27. 5-DMAP through a low-resolution X-ray crystal structure (M. M.-C. Lo).
28. Ruble, J. C., Hoic, D. A. Unpublished results.
29. The corresponding distances for ruthenocene and ferrocene are 3.68 and 3.32 Å, respectively (Hardgrove, G. L.; Templeton, D. H. Acta. Crystallogr. 1959, 12, 28-32; Dunitz, J. D.; Orgel, L. E.; Rich, A. Acta. Crystallogr. 1956, 9, 373-375).
30. The corresponding distances for ruthenocene and ferrocene are 3.68 and 3.32 Å, respectively (Hardgrove, G. L.; Templeton, D. H. Acta. Crystallogr. 1959, 12, 28-32; Dunitz, J. D.; Orgel, L. E.; Rich, A. Acta. Crystallogr. 1956, 9, 373-375).
31. For other catalysts, see: (a) Addition of alcohols to ketenes: Tidwell, T. T. Ketenes; Wiley: New York, 1995. (b) Acylation of alcohols with diketene: Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725.
32. For other catalysts, see: (a) Addition of alcohols to ketenes: Tidwell, T. T. Ketenes; Wiley: New York, 1995. (b) Acylation of alcohols with diketene: Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722-725.
33. The half-life for the corresponding reaction in the presence of 4-dimethylaminoquinoline (5%) is 70 h.
34. The half-life for the corresponding reaction in the presence of 4-dimethylaminoquinoline (1%) is 80 h.
35. Oriyama, T.; Hori, Y.; Imai, K.; Sasaki. R. Tetrahedron Left. 1996, 37, 8543-8546.
36. 5-DMAP that is of sufficient quality to permit a definitive assignment.
37. 5-DMAP can be recovered in essentially quantitative yield at the end of the reaction.
38. Belokin, Y. N.; Bachurina, I. B.; Tararov, V. I.; Saporovskaya, M. B. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1992, 41, 422-429.
39. (-)-Ru-DMAP* can be recovered in essentially quantitative yield at the end of the reaction.
40. Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 5391-5396.
41. (a) Chen, F. M. F.; Kuroda, K.; Bentoiton, N. L. Synthesis 1979, 230.
42. (b) Mohr, F.; Stroschein, F. Chem. Ber. 1909, 42, 2521.
43. Slocum, D. W.; Matusz, M.; Clearfield, A.; Peascoe, R.; Duraj, S. A. J. Macromol. Sci., Chem. 1990, A27, 1405-1414.