Stable dicarbonylcarbene complexes of bis(oxazolinyl)pyridine ruthenium and osmium

Chemistry Letters

Volumn , Issue 12, 1996, Pages 1071-1072

  Nishiyama, Hisao ^a   Aoki, Katsuyuki ^a   Itoh, Hirofumi ^a   Iwamura, Taichiro ^a   Sakata, Naoya ^a   Kurihara, Osamu ^a   Motoyama, Yukihiro ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001698652     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.1071     Document Type: Article

References (23)

1. a) U. Schubert in Advances in Metal Carbene Chemistry, Kulwer Academic Publishers, Dordrecht, (1989).
2. b) M. P. Doyle, Catalytic Asymmetric Synthesis, ed by I. Ojima, VCH Publisher, Inc., New York (1993), p. 63.
3. c) R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley and Sons, Inc., New York (1994), p. 199.
4. a) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, and K. Itoh, J. Am. Chem. Soc., 116, 2223 (1994).
5. b) H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, and K. Itoh, Bull. Chem. Soc. Jpn., 68, 1247 (1995).
6. S.-B. Park, H. Nishiyama, Y. Itoh, and K. Itoh, J. Chem. Soc., Chem. Commun., 1994, 1315.
7. H. Nishiyama, S.-B. Park, and K. Itoh, Chem. Lett., 1995, 599.
8. S.-B. Park, N. Sakata, and H. Nishiyama, Chem. Eur. J., 2, 303 (1996).
9. a) S. A. Matlin, W. J. Lough, L. Chan, D. M. H. Abram, and Z. Zhou, J. Chem. Soc., Chem. Commun., 1984, 1038.
10. b) A. Demonceau, A. F. Noels, J.-L. Costa, and A. J. Hubert, J. Mol. Catal., 58, 21 (1990).
11. c) M. P. Doyle, R. L. Dorow, and W. H. Tamblyn, J. Org. Chem., 47, 4059 (1982).
12. W. A. Herrmann, Chem. Ber., 111, 1077 (1978).
13. a) D. A. Smith, D. N. Reynolds, and L. K. Woo, J. Am. Chem. Soc., 115, 2511 (1993).
14. b) L. K. Woo and D. A. Smith, Organometallics, 11, 2344 (1992).
15. c) J.-P. Djukic, D. A. Smith, V. G. Young, Jr., and L. K. Woo, Organometallics, 13, 3020 (1994).
16. d) J. P. Collman, E. Rose, and G. D. Venburg, J. Chem. Soc., Chem. Commun., 1993, 934.
17. T. Auther and T. A. Stephenson, J. Organomet. Chem., 208, 369 (1981).
18. 3, TMS): δ 0.80 (d, J = 6.8 Hz, 6H), 1.04 (d, J = 6.8 Hz, 6H), 2.56 (m, 2H), 4.40-4.60 (m, 6H), 4.85 (m, 2H), 4.99 (m, 2H), 7.11 (t, J= 7.3 Hz, 1H), 7.38 (d, J = 7.3 Hz, 2H). EA, CHN for 5-7. 6 and 7 were single stereoisomers in terms of prochiral face recognition of propylene and styrene, respectively, even in solutions on the basis of NMR. The coordinated olefins of 5, 6, and 7 do not dissociate. The coordination of the si-face of styrene on 6 was confirmed by single-crystal X-ray analysis, which will be reported in near future.
19. a) M. Regitz, J. Hocker, and A. Liedhegener, Org. Syn. Coll. Vol. 5, John Wiley and Sons, Inc., New York (1973), p. 179.
20. b) W. Ando, T. Yagihara, S. Tozune, I. Imai, J. Suzuki, T. Toyama, S. Nakaido, and T. Migita, J. Org. Chem., 37, 3611 (1972).
21. 2Ru: Found C 43.67, H 4.88, N 7.03%; Calcd C 43.79, H 4.84, N 6.96%.
22. W = 4.8%. The selected bond distances (Å) and angles (deg): Ru(1)-C(18) 1.880(7), C(18)-C(19) 1.499(9), C(18)-C(21) 1.49(10), N(2)-Ru(1)-N(3) 150.7(2), Ru(1)-C(18)-C(19) 121.5(5), Ru(1)-C(18)-C(21) 124.0(5), Cl(1)-Ru(1)-C(18)-C(19) -10.2(5), Cl(2)-Ru(1)-C(18)-C(21)-12.7(6).
23. 13C NMR, 271.0 ppm for Os=C.