Optically active β-ketoiminato cationic cobalt(III) complexes: Efficient catalysts for enantioselective carbonyl-ene reaction of glyoxal derivatives

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1937-1939

  Kezuka, Satoko ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

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ARTICLE;

EID: 0012809298     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015980m     Document Type: Article

References (29)

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2. A zwitterionic intermediate was also proposed for the Lewis acid catalyzed carbonyl-ene reaction: Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555. Snider, B. B.; Phillips, G. B. J. Org. Chem. 1983, 48, 464.
3. A zwitterionic intermediate was also proposed for the Lewis acid catalyzed carbonyl-ene reaction: Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555. Snider, B. B.; Phillips, G. B. J. Org. Chem. 1983, 48, 464.
4. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
5. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
6. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
7. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
8. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
9. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
10. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
11. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
12. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
13. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
14. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K. Pure Appl. Chem. 1996, 68, 639. Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059. Qian, C.; Huang, T. Tetrahedron Lett. 1997, 38, 6721. Qian C.; Huang, T. Tetrahedron: Asymmetry 2000, 11, 2347. For reviews on the carbonyl-ene reaction, see: Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1990, 48, 292. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
15. The ketoiminato cobalt(II) complexes effectively catalyzed the enantioselective borohydride reductions of ketones, imines, and α,β-unsaturated carboxamides and the enantioselective cyclopropanation of styrene derivatives: Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493. Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345.
16. The ketoiminato cobalt(II) complexes effectively catalyzed the enantioselective borohydride reductions of ketones, imines, and α,β-unsaturated carboxamides and the enantioselective cyclopropanation of styrene derivatives: Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493. Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345.
17. The ketoiminato cobalt(II) complexes effectively catalyzed the enantioselective borohydride reductions of ketones, imines, and α,β-unsaturated carboxamides and the enantioselective cyclopropanation of styrene derivatives: Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493. Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345.
18. The ketoiminato cobalt(II) complexes effectively catalyzed the enantioselective borohydride reductions of ketones, imines, and α,β-unsaturated carboxamides and the enantioselective cyclopropanation of styrene derivatives: Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493. Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345.
19. The ketoiminato cobalt(II) complexes effectively catalyzed the enantioselective borohydride reductions of ketones, imines, and α,β-unsaturated carboxamides and the enantioselective cyclopropanation of styrene derivatives: Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493. Yamada, T.; Ohtsuka, Y.; Ikeno, T. Chem. Lett. 1998, 1129. Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345.
20. Yamada, T.; Kezuka, S.; Mita, T.; Ikeno, T. Heterocycles 2000, 52, 1041.
21. (a) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Chem. Lett. 2000, 824.
22. (b) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn., in press.
23. 3 was the most suitable solvent to afford the corresponding homoallylic alcohol in high yield and with high enantioselectivity. The enantioselectivity at 0°C was lower than that at -20°C. Although the enantioselectivity at -40°C was slightly improved, the reaction rate was decreased.
24. Olah, G. A.; Prakash, G. K. S.; Sommer, J. Superacids; John Wiley & Sons: New York, 1985.
25. Fabre, P. L.; Devynck, J.; Tremillon, B. Chem. Rev. 1982, 82, 591. Grondin, J.; Sagnes, R.; Commeyras, A. Bull. Soc. Chim. Fr. 1976, 1779.
26. Fabre, P. L.; Devynck, J.; Tremillon, B. Chem. Rev. 1982, 82, 591. Grondin, J.; Sagnes, R.; Commeyras, A. Bull. Soc. Chim. Fr. 1976, 1779.
27. For the present carbonyl-ene reaction, mono- and trisubstituted alkenes were not reactive enough to the glyoxal derivatives.
28. Ohtani, I.; Kusumi, T.; Kashnan, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
29. The absolute configuration of the resulting pyranone derivatives in the cobalt-complex-catalyzed hetero Diels-Alder reaction was explained by the semiempirical method; ref 6b.