Asymmetric hydrogenation of cyclic α,β-unsaturated ketones to chiral allylic alcohols

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 467-468

  Ohkuma, Takeshi ^a   Ikehira, Hideyuki ^a   Ikariya, Takao ^a   Noyori, Ryoji ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000143557     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6141     Document Type: Article

References (29)

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2. Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872.
3. (a) Krishnamurthy, S.; Brown, H. C. J. Am. Chem. Soc. 1976, 98, 3383.
4. (b) Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159.
5. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.
6. For a recent account, see: Noyori, R. Acta Chem. Scand. 1996, 50, 380.
7. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994; Chapter 2.
8. 2-DIOP System. See: Spogliarich, R.; Vidotto, S.; Farnetti, E.; Graziani, M.; Gulati, N. V. Tetrahedron: Asymmetry 1992, 3, 1001.
9. For catalytic asymmetric hydroboration, see: Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611, and references therein.
10. Hydrosilylation: Kogure, T.; Ojima, I. J. Organomet. Chem. 1982, 234, 249.
11. Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
12. (a) Pikul, S.; Corey, E. J. Org. Synth. 1993, 71, 22.
13. (b) Mangeney, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, J. Synthesis 1988, 255.
14. 3OH)).
15. Mori, K.; Puapoomchareon, P. Liebigs Ann. Chem. 1991, 1053.
16. The 2-cyclohexen-1-one and 2-cyclohexen-1-ol numbering (IUPAC) is used throughout this paper.
17. The absolute configuration and enantiomeric purity were not determined.
18. Balavoine, G.; Moradpour, A.; Kagan, H. B. J. Am. Chem. Soc. 1974, 96, 5152.
19. Ireland, R. E.; Bey, P. Org. Synth. Coll. Vol. 6 1988, 459.
20. Fortunato, J. M.; Ganem, B. J. Org. Chem. 1976, 41, 2194.
21. Luche claimed that the hydride reduction proceeds with perfect cis selectivity. See: Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
22. For hydrogenation of 3 with transition-metal complex catalysts, see: (a) Daeuble, J. F.; Stryker, J. M. In Catalysis of Organic Reactions; Scaros, M. G., Prunier, M. L., Eds.; Dekker: New York, 1995; p 235.
23. (b) Mestroni, G.; Spogliarich, R.; Camus, A.; Martinelli, F.; Zassinovich, G. J. Organomet. Chem. 1978, 157, 345. Also see ref. 7.
24. n-(R,R)-DPEN system (ketone:Ru:diamine:KOH = 500:1:1:2, 2-propanol, 4 atm, 28 °C, 1 h) gave a mixture of (R)-2-cyclohexen-1-ol (58% ee, 65% yield), cyclohexanol (2%), and polymeric material (30%).
25. n-(R,R)-DPEN system (ketone:Ru:diamine:KOH = 500:1:1:2, 2-propanol, 4 atm, 28 °C, 2 h) afforded (S)-4,4-dimethyl-2-cyclohexen-1-ol with 47% ee in 100% yield.
26. n-(R,R)-DPEN system (ketone:Ru:diamine:KOH = 500:1:1:2, 6:1 2-propanol-toluene, 8 atm, 28 °C, 18 h) gave (R)-3-methyl-2-cyclohexenol with 45% ee in 99% yield.
27. For catalytic access to 2-unsubstituted 2-cyclohexen-1-ols with high enetiomeric purity, see: (a) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708.
28. (b) Hashiguchi, S.; Fujii, A.; Haack, K.-J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem. 1997, 109, 300;
29. Angew. Chem., Int. Ed. Engl. 1997, 36, 288.