Optically active cationic cobalt(III) complexes: Highly efficient catalysts for enantioselective hetero Diels-Alder reaction

Chemistry Letters

Volumn , Issue 7, 2000, Pages 824-825

  Kezuka, Satoko ^a   Mita, Tsuyoshi ^a   Ohtsuki, Natsuki ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034339610     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.824     Document Type: Article

References (24)

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2. S. E. Schaus, J. Brånalt, and E. N. Jacobsen, J. Org. Chem., 63, 403 (1998); Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 63, 2456 (1998); J. Mihata, T. Hamada, T. Takeda R. Irie, and T. Katsuki, Synlett, 1999, 1160; Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, and H. Yamamoto, Tetrahedron. 50, 979 (1994); Y. Motoyama, M. Terada, and K. Mikami, Synlett, 1995, 967; K. B. Simonsen, N. Svenstrup, M. Roberson, and K. A. Jørgensen, Chem. Eur. J., 6, 123 (2000); S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, and K. A. Jørgensen, J. Am. Chem. Soc., 120, 8599 (1998); T. Hamamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79; G. E. Keck, X,-Y. Li, and D. Krishnamurthy, J. Org. Chem., 60, 5998 (1995).
3. S. E. Schaus, J. Brånalt, and E. N. Jacobsen, J. Org. Chem., 63, 403 (1998); Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 63, 2456 (1998); J. Mihata, T. Hamada, T. Takeda R. Irie, and T. Katsuki, Synlett, 1999, 1160; Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, and H. Yamamoto, Tetrahedron. 50, 979 (1994); Y. Motoyama, M. Terada, and K. Mikami, Synlett, 1995, 967; K. B. Simonsen, N. Svenstrup, M. Roberson, and K. A. Jørgensen, Chem. Eur. J., 6, 123 (2000); S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, and K. A. Jørgensen, J. Am. Chem. Soc., 120, 8599 (1998); T. Hamamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79; G. E. Keck, X,-Y. Li, and D. Krishnamurthy, J. Org. Chem., 60, 5998 (1995).
4. S. E. Schaus, J. Brånalt, and E. N. Jacobsen, J. Org. Chem., 63, 403 (1998); Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 63, 2456 (1998); J. Mihata, T. Hamada, T. Takeda R. Irie, and T. Katsuki, Synlett, 1999, 1160; Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, and H. Yamamoto, Tetrahedron. 50, 979 (1994); Y. Motoyama, M. Terada, and K. Mikami, Synlett, 1995, 967; K. B. Simonsen, N. Svenstrup, M. Roberson, and K. A. Jørgensen, Chem. Eur. J., 6, 123 (2000); S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, and K. A. Jørgensen, J. Am. Chem. Soc., 120, 8599 (1998); T. Hamamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79; G. E. Keck, X,-Y. Li, and D. Krishnamurthy, J. Org. Chem., 60, 5998 (1995).
5. S. E. Schaus, J. Brånalt, and E. N. Jacobsen, J. Org. Chem., 63, 403 (1998); Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 63, 2456 (1998); J. Mihata, T. Hamada, T. Takeda R. Irie, and T. Katsuki, Synlett, 1999, 1160; Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, and H. Yamamoto, Tetrahedron. 50, 979 (1994); Y. Motoyama, M. Terada, and K. Mikami, Synlett, 1995, 967; K. B. Simonsen, N. Svenstrup, M. Roberson, and K. A. Jørgensen, Chem. Eur. J., 6, 123 (2000); S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, and K. A. Jørgensen, J. Am. Chem. Soc., 120, 8599 (1998); T. Hamamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79; G. E. Keck, X,-Y. Li, and D. Krishnamurthy, J. Org. Chem., 60, 5998 (1995).
6. S. E. Schaus, J. Brånalt, and E. N. Jacobsen, J. Org. Chem., 63, 403 (1998); Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 63, 2456 (1998); J. Mihata, T. Hamada, T. Takeda R. Irie, and T. Katsuki, Synlett, 1999, 1160; Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, and H. Yamamoto, Tetrahedron. 50, 979 (1994); Y. Motoyama, M. Terada, and K. Mikami, Synlett, 1995, 967; K. B. Simonsen, N. Svenstrup, M. Roberson, and K. A. Jørgensen, Chem. Eur. J., 6, 123 (2000); S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, and K. A. Jørgensen, J. Am. Chem. Soc., 120, 8599 (1998); T. Hamamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79; G. E. Keck, X,-Y. Li, and D. Krishnamurthy, J. Org. Chem., 60, 5998 (1995).
7. S. E. Schaus, J. Brånalt, and E. N. Jacobsen, J. Org. Chem., 63, 403 (1998); Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 63, 2456 (1998); J. Mihata, T. Hamada, T. Takeda R. Irie, and T. Katsuki, Synlett, 1999, 1160; Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, and H. Yamamoto, Tetrahedron. 50, 979 (1994); Y. Motoyama, M. Terada, and K. Mikami, Synlett, 1995, 967; K. B. Simonsen, N. Svenstrup, M. Roberson, and K. A. Jørgensen, Chem. Eur. J., 6, 123 (2000); S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, and K. A. Jørgensen, J. Am. Chem. Soc., 120, 8599 (1998); T. Hamamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79; G. E. Keck, X,-Y. Li, and D. Krishnamurthy, J. Org. Chem., 60, 5998 (1995).
8. S. E. Schaus, J. Brånalt, and E. N. Jacobsen, J. Org. Chem., 63, 403 (1998); Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 63, 2456 (1998); J. Mihata, T. Hamada, T. Takeda R. Irie, and T. Katsuki, Synlett, 1999, 1160; Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, and H. Yamamoto, Tetrahedron. 50, 979 (1994); Y. Motoyama, M. Terada, and K. Mikami, Synlett, 1995, 967; K. B. Simonsen, N. Svenstrup, M. Roberson, and K. A. Jørgensen, Chem. Eur. J., 6, 123 (2000); S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, and K. A. Jørgensen, J. Am. Chem. Soc., 120, 8599 (1998); T. Hamamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79; G. E. Keck, X,-Y. Li, and D. Krishnamurthy, J. Org. Chem., 60, 5998 (1995).
9. S. E. Schaus, J. Brånalt, and E. N. Jacobsen, J. Org. Chem., 63, 403 (1998); Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 63, 2456 (1998); J. Mihata, T. Hamada, T. Takeda R. Irie, and T. Katsuki, Synlett, 1999, 1160; Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, and H. Yamamoto, Tetrahedron. 50, 979 (1994); Y. Motoyama, M. Terada, and K. Mikami, Synlett, 1995, 967; K. B. Simonsen, N. Svenstrup, M. Roberson, and K. A. Jørgensen, Chem. Eur. J., 6, 123 (2000); S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, and K. A. Jørgensen, J. Am. Chem. Soc., 120, 8599 (1998); T. Hamamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79; G. E. Keck, X,-Y. Li, and D. Krishnamurthy, J. Org. Chem., 60, 5998 (1995).
10. Their manganese(III) complex catalysts; T. Nagata, K. Imagawa, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 1455 and 3421 (1995). The corresponding cobalt(II) complex catalysts; T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem. Lett., 1997, 493; T. Yamada, Y. Ohtsuka, and T. Ikeno, Chem. Lett., 1998. 1129. Recently, it was reported that their derivatives catalyzed the enantioselective cyclopropanation of styrene derivatives; T. Yamada, T. Ikeno, and M. Sato, Chem. Lett., 1999, 1345.
11. Their manganese(III) complex catalysts; T. Nagata, K. Imagawa, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 1455 and 3421 (1995). The corresponding cobalt(II) complex catalysts; T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem. Lett., 1997, 493; T. Yamada, Y. Ohtsuka, and T. Ikeno, Chem. Lett., 1998. 1129. Recently, it was reported that their derivatives catalyzed the enantioselective cyclopropanation of styrene derivatives; T. Yamada, T. Ikeno, and M. Sato, Chem. Lett., 1999, 1345.
12. Their manganese(III) complex catalysts; T. Nagata, K. Imagawa, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 1455 and 3421 (1995). The corresponding cobalt(II) complex catalysts; T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem. Lett., 1997, 493; T. Yamada, Y. Ohtsuka, and T. Ikeno, Chem. Lett., 1998. 1129. Recently, it was reported that their derivatives catalyzed the enantioselective cyclopropanation of styrene derivatives; T. Yamada, T. Ikeno, and M. Sato, Chem. Lett., 1999, 1345.
13. Their manganese(III) complex catalysts; T. Nagata, K. Imagawa, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 1455 and 3421 (1995). The corresponding cobalt(II) complex catalysts; T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem. Lett., 1997, 493; T. Yamada, Y. Ohtsuka, and T. Ikeno, Chem. Lett., 1998. 1129. Recently, it was reported that their derivatives catalyzed the enantioselective cyclopropanation of styrene derivatives; T. Yamada, T. Ikeno, and M. Sato, Chem. Lett., 1999, 1345.
14. Their manganese(III) complex catalysts; T. Nagata, K. Imagawa, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 1455 and 3421 (1995). The corresponding cobalt(II) complex catalysts; T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem. Lett., 1997, 493; T. Yamada, Y. Ohtsuka, and T. Ikeno, Chem. Lett., 1998. 1129. Recently, it was reported that their derivatives catalyzed the enantioselective cyclopropanation of styrene derivatives; T. Yamada, T. Ikeno, and M. Sato, Chem. Lett., 1999, 1345.
15. T. Yamada, S. Kezuka, T. Mita, and T. Ikeno, Heterocycles, 52 1041 (2000).
16. T. Yamada, T. Nagata, T. Ikeno, Y. Ohtsuka, A. Sagara, and T. Mukaiyama, Inorg. Chim. Acta, 296, 86 (1999).
17. T. Nagata, K. Imagawa, T. Yamada, and T. Mukaiyama, Chem. Lett., 1994, 1259.
18. M. E. Furrow, S. E. Schaus, and E. N. Jacobsen, J. Org. Chem., 63, 6776 (1998).
19. It was reported that the Co(II) complexes with salen-type ligands showed better enantioselectivity in the hetero Diels-Alder reaction than the corresponding Co(III) complexes; L.-S. Li, Y. Wu, Y.-J. Xia, and Y.-L. Wu, Tetrahedron: Asym., 9, 2271 (1998).
20. Preparation of cobalt(III) triflate complex: To a solution of the cobalt complex B-I (259.9 mg, 0.295 mmol) in dichloromethane (10.0 mL) was added AgOTf (84.4 mg, 0.329 mmol) in dichloromethane (1.0 mL). The mixture was stirred for 1.5 h and the resulting AgI was filtered off. The crude product was purified by reprecipitation from dichloromethane/hexane to afford the cationic cobalt(III) complex B-OTf (231.4 mg) in 87% yield as a green solid. (matrix presented)
21. 3 solution, a standard workup and chromatography on silica gel afforded 2,3-dihydro-2-(4-nitrophenyl)-4H-pyran-4-one (102.5 mg) in 94% yield. The optical yield of the product was determined by HPLC analysis (Daicel Chiralcel OD-H, IPA 10% in hexane) to be 94% ee.
22. Aryl aldehydes with ortho-halide or ortho-alkoxide reacted with dienes faster than that with the corresponging aldehydes of para-substitution. A detailed study of these observations is currently under way.
23. (S)-2-Aryl-dihydropyran-4-ones were obtained corresponding to the (S,S)-cobalt complex catalysts. 2-(p-Nitrophenyl)dihydropyran-4-one: R. F. Lowe and R. J. Stoodley, Tetrahedron Lett., 35, 6351 (1994). 2-Phenyldihydropyran-4-one: E. J. Corey, C. L. Cywin, and T. D. Roper, Tetrahedron Lett., 33, 6907 (1992).
24. (S)-2-Aryl-dihydropyran-4-ones were obtained corresponding to the (S,S)-cobalt complex catalysts. 2-(p-Nitrophenyl)dihydropyran-4-one: R. F. Lowe and R. J. Stoodley, Tetrahedron Lett., 35, 6351 (1994). 2-Phenyldihydropyran-4-one: E. J. Corey, C. L. Cywin, and T. D. Roper, Tetrahedron Lett., 33, 6907 (1992).