The Catalyst Precursor, Catalyst, and Intermediate in the RuII-Promoted Asymmetric Hydrogen Transfer between Alcohols and Ketones

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 3, 1997, Pages 285-288

  Haack, Karl Josef ^a   Hashiguchi, Shohei ^a   Fujii, Akio ^a   Ikariya, Takao ^a   Noyori, Ryoji ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Chirality; Homogeneous catalysis; Hydrido complexes; Ruthenium

Indexed keywords

EID: 0030984352     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199702851     Document Type: Article

References (27)

1. a) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562-7563;
2. b) J. Takehara, S. Hashiguchi, A. Fujii, S. Inoue, T. Ikariya, R. Noyori, Chem. Commun. 1996, 233-234;
3. c) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087-1089;
4. d) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, in press.
5. S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300-303; Angew. Chem. Int. Ed. Engl. 1997, 36, 288-290.
6. S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300-303; Angew. Chem. Int. Ed. Engl. 1997, 36, 288-290.
7. a) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521-2522;
8. b) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori, ibid. 1996, 118, 4916-4917.
9. J. Halpern in Asymmetric Synthesis, Vol. 5 (Ed. J. D. Morrison), Academic Press, New York, 1985, Chapter 2.
10. Kα). The structures were solved with PATTY and DIRDIF94 [5b]. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-149. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code + (1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk), on quoting the full journal citation; b) P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel, J. M. M. Smits, C. Smykalla, The DIRDIF Program System, Technical Report of the Cristallographic Laboratory, University of Nijmegen, The Netherlands, 1994.
11. For the notation of the absolute configuration, see: a) C. Lecomte, Y. Dusausoy, J. Protas, J. Tirouflet, A. Dormond, J. Organomet. Chem. 1974, 73, 67-76; b) K. Stanley, M. C. Baird, J. Am. Chem. Soc. 1975, 97, 6598-6599.
12. For the notation of the absolute configuration, see: a) C. Lecomte, Y. Dusausoy, J. Protas, J. Tirouflet, A. Dormond, J. Organomet. Chem. 1974, 73, 67-76; b) K. Stanley, M. C. Baird, J. Am. Chem. Soc. 1975, 97, 6598-6599.
13. a) M. D. Fryzuk, P. A. MacNeil, S. J. Rettig, J. Am. Chem. Soc. 1987, 109, 2803-2812;
14. b) M. D. Fryzuk, C. D. Montgomery, Coord. Chem. Rev. 1989, 95, 1-40;
15. c) M. D. Fryzuk, C. D. Montgomery, S. J. Rettig, Organometallics 1991, 10, 467-473.
16. M. L. Tobe, Adv. Inorg. Bioinorg. Meth. 1983, 2, 1-94.
17. T. J. Johnson, J. C. Huffman, K. G. Caulton, J. Am. Chem. Soc. 1992, 114, 2725-2726.
18. J. F. Hartwig, R. A. Andersen, R. G. Bergman, Organometallics 1991, 10, 1875-1887; M. J. Burn, M. G. Fickes, F. J. Hollander, R. G. Bergman, ibid. 1995, 14, 137-150; A. Anillo, C. Barrio, S. Garci'a-Granda, R. Obeso-Rosete, J. Chem. Soc. Dalton Trans. 1993, 1125-1130.
19. J. F. Hartwig, R. A. Andersen, R. G. Bergman, Organometallics 1991, 10, 1875-1887; M. J. Burn, M. G. Fickes, F. J. Hollander, R. G. Bergman, ibid. 1995, 14, 137-150; A. Anillo, C. Barrio, S. Garci'a-Granda, R. Obeso-Rosete, J. Chem. Soc. Dalton Trans. 1993, 1125-1130.
20. J. F. Hartwig, R. A. Andersen, R. G. Bergman, Organometallics 1991, 10, 1875-1887; M. J. Burn, M. G. Fickes, F. J. Hollander, R. G. Bergman, ibid. 1995, 14, 137-150; A. Anillo, C. Barrio, S. Garci'a-Granda, R. Obeso-Rosete, J. Chem. Soc. Dalton Trans. 1993, 1125-1130.
21. A. A. Danopoulos, G. Wilkinson, B. Hussain-Bates, M. B. Hursthouse, Polyhedron 1992, 11, 2961-2964; A. K. Burrell, A. J. Steedman, J. Chem. Soc. Chem. Commun. 1995, 2109-2110.
22. A. A. Danopoulos, G. Wilkinson, B. Hussain-Bates, M. B. Hursthouse, Polyhedron 1992, 11, 2961-2964; A. K. Burrell, A. J. Steedman, J. Chem. Soc. Chem. Commun. 1995, 2109-2110.
23. K. G. Caulton, New J. Chem. 1994, 18, 25-41.
24. E. S. Shubina, N. V. Belkova, A. N. Krylov, E. V. Vorontsov, L. M. Epstein, D. G. Gusev, M. Niedermann, H. Berke, J. Am. Chem. Soc. 1996, 118, 1105-1112.
25. V. J. Sciner, Jr., D. Whittaker, J. Am. Chem. Soc. 1969, 91, 394-398.
26. M. A. Bennett, T.-N. Huang, T. W. Matheson, A. K. Smith, Inorg. Synth. 1982, 21, 74-78.
27. T. Oda, R. Irie, T. Katsuki, H. Okawa, Synlett 1992, 641-643.