Enantiofacially selective olefin coordination of α,β-unsaturated carbonyl compounds to chiral bis(oxazolinyl)pyridineruthenium fragments

Organometallics

Volumn 17, Issue 7, 1998, Pages 1251-1253

  Motoyama, Yukihiro ^a   Murata, Kiyoshi ^a   Kurihara, Osamu ^a   Naitoh, Tomonari ^a   Aoki, Katsuyuki ^a   Nishiyama, Hisao ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 11644315338     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om971034r     Document Type: Article

References (33)

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7. Reviews: (a) Morrison, J. D. Asymmetric Synthesis; Academic Press: New York, 1984; Vol. 3B. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5. (c) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, The Netherlands, 1986. For Lewis acid carbonyl complexation, see: (d) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256. (e) Shambayati, S.; Schreiber, S. L. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1.
8. Reviews: (a) Morrison, J. D. Asymmetric Synthesis; Academic Press: New York, 1984; Vol. 3B. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5. (c) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, The Netherlands, 1986. For Lewis acid carbonyl complexation, see: (d) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256. (e) Shambayati, S.; Schreiber, S. L. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1.
9. Reviews: (a) Morrison, J. D. Asymmetric Synthesis; Academic Press: New York, 1984; Vol. 3B. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5. (c) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, The Netherlands, 1986. For Lewis acid carbonyl complexation, see: (d) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256. (e) Shambayati, S.; Schreiber, S. L. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1.
10. Reviews: (a) Morrison, J. D. Asymmetric Synthesis; Academic Press: New York, 1984; Vol. 3B. (b) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5. (c) Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, The Netherlands, 1986. For Lewis acid carbonyl complexation, see: (d) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256. (e) Shambayati, S.; Schreiber, S. L. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1.
11. Review: Gladysz, J. A.; Boone, B. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 550, and references therein.
12. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
13. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
14. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
15. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
16. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
17. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
18. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
19. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
20. Recent representative papers: (a) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253. (b) Bodner, G. S.; Peng, T.-S.; Arif, A. M.; Gladysz, J. A. Organometallics 1990, 9, 1191. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2686. (c) Schmid, G.; Kilanowski, B.; Boese, R.; Blaser, D. Chem. Ber. 1993, 126, 899. (d) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; de Felice, V. Organometallics 1995, 14, 1152. (e) Jedlicka, B.; Rulke, R. E.; Weissensteiner, W.; Fernandez-Galan, R.; Jalon, F. A.; Manzano, B. R.; Rodriguez-de la Fuente, J.; Veldman, N.; Kooijman, H.; Spek, A. L. J. Organomet. Chem. 1996, 516, 97. (f) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517. (g) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156. (h) Erickson, L. E.; Hayes, P.; Hooper, J. J.; Morris, K. F.; Newbrough, K. F.; van Os, M.; Slangen, P. Inorg. Chem. 1997, 36, 284.
21. (a) Quiros Mendez, N.; Mayne, C. L.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 2323.
22. (b) Wang, Y.; Agbossou, F.; Dalton, D. M.; Liu, Y.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2699.
23. Hollis, T. K.; Odenkirk, W.; Robinson, N. P.; Whelan, J.; Bosnich, B. Tetrahedron 1993, 49, 5415, and references therein.
24. (a) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
25. (b) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
26. 4-90°) (2a′) was carried out to show that isomer 2a proved to be more stable than 2a′ by 1.48 eV (34.2 kcal/mol), see Supporting Information for input data for EHMO calculation.
27. 13C NMR spectra of these complexes show a single set of diastereotopic vinylic proton and carbon resonances, see: Nishiyama, H.; Aoki, K.; Itoh, H.; Iwamura, T.; Kurihara, O.; Motoyama, Y. Chem. Lett. 1996, 1071.
28. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 223.
29. 3)(olefin) complexes exist in σ O=C, π O=C, and π C=C complex forms. These conformations are highly dependent on the reaction temperature and substitution patterns of the α,β-unsaturated carbonyl compounds, see: ref 5b.
30. From the ab initio calculations of free (uncomplexed) acrolein, the s-trans conformation is preferred over the s-cis conformation. In the case of methyl acrylate, the s-cis/syn conformer is more stable than the s-trans/syn conformer, see: Loncharich, R. J.; Schwartz, R.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 14.
31. 2 fragments were slowly dissociated in solution at 25 °C.
32. w = 0.042. Selected bond distances (Å) and angles (deg): Ru(1)-N(1) 2.02(2), Ru(1)-N(2) 2.13(2), Ru(1)-N(3) 2.16(2), Ru(1)-C(14) 2.20(1), Ru(1)-C(15) 2.24(2), C(14)-C(15) 1.42(4), C(16)-O(3) 1.20(2), N(2)-Ru(1)-N(3) 152.5(6), Cl(1)-Ru(1)-Cl(2) 176.3(2).
33. 2-dimethyl fumarate) complex, which has no chloride at the apical position on Pt, the conformation of coordinated dimethyl fumarate was s-cis, see: Albano, V. G.; Castellari, C.; Monari, M.; De Felice, V.; Panunzi, A.; Ruffo, F. Organometallics 1996, 15, 4012.