Stereoselective hydrogenation of simple ketones catalyzed by ruthenium(II) complexes

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4872-4873

  Ohkuma, Takeshi ^a   Ooka, Hirohito ^a   Yamakawa, Masashi ^a,b   Ikariya, Takao ^a   Noyori, Ryoji ^a,c  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b KINJO GAKUIN UNIVERSITY   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041768214     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960997h     Document Type: Article

References (37)

1. Selected reviews: (a) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567-607. (b) El-Khawaga, A. M.; Hoffmann, H. M. R. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3967-3987. (c) Davis, A. P. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3988-4048. (d) Krohn, K. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 4099-4142. See also: (e) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Burkhardt, E. R.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1994, 59, 6378-6385. (f) Barden, M. C.; Schwartz, J. J. Org. Chem. 1995, 60, 5963-5965,
2. Selected reviews: (a) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567-607. (b) El-Khawaga, A. M.; Hoffmann, H. M. R. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3967-3987. (c) Davis, A. P. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3988-4048. (d) Krohn, K. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 4099-4142. See also: (e) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Burkhardt, E. R.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1994, 59, 6378-6385. (f) Barden, M. C.; Schwartz, J. J. Org. Chem. 1995, 60, 5963-5965,
3. Selected reviews: (a) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567-607. (b) El-Khawaga, A. M.; Hoffmann, H. M. R. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3967-3987. (c) Davis, A. P. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3988-4048. (d) Krohn, K. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 4099-4142. See also: (e) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Burkhardt, E. R.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1994, 59, 6378-6385. (f) Barden, M. C.; Schwartz, J. J. Org. Chem. 1995, 60, 5963-5965,
4. Selected reviews: (a) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567-607. (b) El-Khawaga, A. M.; Hoffmann, H. M. R. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3967-3987. (c) Davis, A. P. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3988-4048. (d) Krohn, K. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 4099-4142. See also: (e) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Burkhardt, E. R.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1994, 59, 6378-6385. (f) Barden, M. C.; Schwartz, J. J. Org. Chem. 1995, 60, 5963-5965,
5. Selected reviews: (a) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567-607. (b) El-Khawaga, A. M.; Hoffmann, H. M. R. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3967-3987. (c) Davis, A. P. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3988-4048. (d) Krohn, K. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 4099-4142. See also: (e) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Burkhardt, E. R.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1994, 59, 6378-6385. (f) Barden, M. C.; Schwartz, J. J. Org. Chem. 1995, 60, 5963-5965,
6. Selected reviews: (a) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567-607. (b) El-Khawaga, A. M.; Hoffmann, H. M. R. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3967-3987. (c) Davis, A. P. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3988-4048. (d) Krohn, K. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 4099-4142. See also: (e) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Burkhardt, E. R.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1994, 59, 6378-6385. (f) Barden, M. C.; Schwartz, J. J. Org. Chem. 1995, 60, 5963-5965,
7. Selectride reagents: (a) Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159-7161. (b) Krishnamurthy, S.; Brown, H. C. J. Am. Chem. Soc. 1976, 98, 3383-3384.
8. Selectride reagents: (a) Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159-7161. (b) Krishnamurthy, S.; Brown, H. C. J. Am. Chem. Soc. 1976, 98, 3383-3384.
9. Reviews on stereoselective hydrogenation: (a) Rylander, P. Catalytic Hydrogenation in Organic Syntheses; Academic Press: New York, 1979; Chapter 6. (b) Harada, K.; Munegumi, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, pp 139-158.
10. Reviews on stereoselective hydrogenation: (a) Rylander, P. Catalytic Hydrogenation in Organic Syntheses; Academic Press: New York, 1979; Chapter 6. (b) Harada, K.; Munegumi, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, pp 139-158.
11. Examples of other catalytic stereoselective methods. Transfer hydrogenation: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785-791. (b) Konishi, K.; Aida, T.; Inoue, S. J. Org. Chem. 1990, 55, 816-820. Hydrosilylation: (c) Ojima, I.; Nihonyanagi, M.; Nagai, Y. Bull. Chem. Soc. Jpn. 1972, 45, 3722. (d) Semmelhack, M. F.; Misra, R. N. J. Org. Chem. 1982, 47, 2469-2471. (e) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5405-5415. Hydrostannation: (f) Quintard, J.-P.; Pereyre, M. Bull. Soc. Chim. Fr. 1972, 1950-1955.
12. Examples of other catalytic stereoselective methods. Transfer hydrogenation: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785-791. (b) Konishi, K.; Aida, T.; Inoue, S. J. Org. Chem. 1990, 55, 816-820. Hydrosilylation: (c) Ojima, I.; Nihonyanagi, M.; Nagai, Y. Bull. Chem. Soc. Jpn. 1972, 45, 3722. (d) Semmelhack, M. F.; Misra, R. N. J. Org. Chem. 1982, 47, 2469-2471. (e) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5405-5415. Hydrostannation: (f) Quintard, J.-P.; Pereyre, M. Bull. Soc. Chim. Fr. 1972, 1950-1955.
13. Examples of other catalytic stereoselective methods. Transfer hydrogenation: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785-791. (b) Konishi, K.; Aida, T.; Inoue, S. J. Org. Chem. 1990, 55, 816-820. Hydrosilylation: (c) Ojima, I.; Nihonyanagi, M.; Nagai, Y. Bull. Chem. Soc. Jpn. 1972, 45, 3722. (d) Semmelhack, M. F.; Misra, R. N. J. Org. Chem. 1982, 47, 2469-2471. (e) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5405-5415. Hydrostannation: (f) Quintard, J.-P.; Pereyre, M. Bull. Soc. Chim. Fr. 1972, 1950-1955.
14. Examples of other catalytic stereoselective methods. Transfer hydrogenation: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785-791. (b) Konishi, K.; Aida, T.; Inoue, S. J. Org. Chem. 1990, 55, 816-820. Hydrosilylation: (c) Ojima, I.; Nihonyanagi, M.; Nagai, Y. Bull. Chem. Soc. Jpn. 1972, 45, 3722. (d) Semmelhack, M. F.; Misra, R. N. J. Org. Chem. 1982, 47, 2469-2471. (e) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5405-5415. Hydrostannation: (f) Quintard, J.-P.; Pereyre, M. Bull. Soc. Chim. Fr. 1972, 1950-1955.
15. Examples of other catalytic stereoselective methods. Transfer hydrogenation: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785-791. (b) Konishi, K.; Aida, T.; Inoue, S. J. Org. Chem. 1990, 55, 816-820. Hydrosilylation: (c) Ojima, I.; Nihonyanagi, M.; Nagai, Y. Bull. Chem. Soc. Jpn. 1972, 45, 3722. (d) Semmelhack, M. F.; Misra, R. N. J. Org. Chem. 1982, 47, 2469-2471. (e) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5405-5415. Hydrostannation: (f) Quintard, J.-P.; Pereyre, M. Bull. Soc. Chim. Fr. 1972, 1950-1955.
16. Examples of other catalytic stereoselective methods. Transfer hydrogenation: (a) Henbest, H. B.; Mitchell, T. R. B. J. Chem. Soc. C 1970, 785-791. (b) Konishi, K.; Aida, T.; Inoue, S. J. Org. Chem. 1990, 55, 816-820. Hydrosilylation: (c) Ojima, I.; Nihonyanagi, M.; Nagai, Y. Bull. Chem. Soc. Jpn. 1972, 45, 3722. (d) Semmelhack, M. F.; Misra, R. N. J. Org. Chem. 1982, 47, 2469-2471. (e) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5405-5415. Hydrostannation: (f) Quintard, J.-P.; Pereyre, M. Bull. Soc. Chim. Fr. 1972, 1950-1955.
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35. Gaussian 94, Revision B.1: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
36. A 5 mmol-scale reaction. [Ketonel = 0.8 M, ketone:Ru:diamine: KOH = 500;1:1:20, 28°C.
37. Atomic coordinates for (1R,2R)- and (1S,2R)-2-isopropylcyclohexyl (R)-N-[1′-(1-naphthyl)ethyl]carbamate have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.