The first highly enantioselective catalytic hetero-Diels-Alder reaction of ketones

Chemical Communications

Volumn , Issue 22, 1997, Pages 2169-2170

  Johannsen, Mogens ^a   Yao, Sulan ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002816322     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a706463b     Document Type: Article

References (21)

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2. R. R. Schmidt. Acc. Chem. Res., 1986, 19, 250; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, 1987.
3. M. Bednarski, C. Maring and S. Danishefsky, Tetrahedron Lett., 1983, 3451.
4. K. Narasaka, M. Inoue and N. Okada, Chem. Lett., 1986, 1109; H. Waldmann, Synthesis, 1994, 535; K. Narasaka, Synthesis, 1991, 1; K. Maruoka and H. Yamamoto, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 413; H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007.
5. K. Narasaka, M. Inoue and N. Okada, Chem. Lett., 1986, 1109; H. Waldmann, Synthesis, 1994, 535; K. Narasaka, Synthesis, 1991, 1; K. Maruoka and H. Yamamoto, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 413; H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007.
6. K. Narasaka, M. Inoue and N. Okada, Chem. Lett., 1986, 1109; H. Waldmann, Synthesis, 1994, 535; K. Narasaka, Synthesis, 1991, 1; K. Maruoka and H. Yamamoto, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 413; H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007.
7. K. Narasaka, M. Inoue and N. Okada, Chem. Lett., 1986, 1109; H. Waldmann, Synthesis, 1994, 535; K. Narasaka, Synthesis, 1991, 1; K. Maruoka and H. Yamamoto, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 413; H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007.
8. K. Narasaka, M. Inoue and N. Okada, Chem. Lett., 1986, 1109; H. Waldmann, Synthesis, 1994, 535; K. Narasaka, Synthesis, 1991, 1; K. Maruoka and H. Yamamoto, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 413; H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007.
9. G. E. Keck, X.-Y. Li and D. Krishnamurthy, J. Org. Chem., 1995, 60, 5998; K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310; T. Hanamoto, H. Furuno and J. Inanaga, Synlett, 1997, 79; Q. Gao, T. Maruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; A. Togni, Organometallics, 1990, 9, 3106; Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563.
10. G. E. Keck, X.-Y. Li and D. Krishnamurthy, J. Org. Chem., 1995, 60, 5998; K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310; T. Hanamoto, H. Furuno and J. Inanaga, Synlett, 1997, 79; Q. Gao, T. Maruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; A. Togni, Organometallics, 1990, 9, 3106; Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563.
11. G. E. Keck, X.-Y. Li and D. Krishnamurthy, J. Org. Chem., 1995, 60, 5998; K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310; T. Hanamoto, H. Furuno and J. Inanaga, Synlett, 1997, 79; Q. Gao, T. Maruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; A. Togni, Organometallics, 1990, 9, 3106; Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563.
12. G. E. Keck, X.-Y. Li and D. Krishnamurthy, J. Org. Chem., 1995, 60, 5998; K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310; T. Hanamoto, H. Furuno and J. Inanaga, Synlett, 1997, 79; Q. Gao, T. Maruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; A. Togni, Organometallics, 1990, 9, 3106; Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563.
13. G. E. Keck, X.-Y. Li and D. Krishnamurthy, J. Org. Chem., 1995, 60, 5998; K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310; T. Hanamoto, H. Furuno and J. Inanaga, Synlett, 1997, 79; Q. Gao, T. Maruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; A. Togni, Organometallics, 1990, 9, 3106; Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563.
14. G. E. Keck, X.-Y. Li and D. Krishnamurthy, J. Org. Chem., 1995, 60, 5998; K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310; T. Hanamoto, H. Furuno and J. Inanaga, Synlett, 1997, 79; Q. Gao, T. Maruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; A. Togni, Organometallics, 1990, 9, 3106; Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563.
15. (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757;
16. (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321;
17. (c) S. Yao, M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 1, 1997, 1234;
18. (d) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183.
19. A. Graven, M. Johannsen and K. A. Jørgensen, Chem. Commun., 1996, 2373.
20. To the best of our knowledge this is the only other paper on enantioselective HDA reactions with ketones, albeit with modest ee: M. Quimpére and K. Jankowski, J. Chem. Soc., Chem. Commun., 1987, 676. See also P. C. B. Page, P. H. Williams, E. W. Collington and H. Finch, J. Chem. Soc., Chem. Commun., 1987, 756.
21. To the best of our knowledge this is the only other paper on enantioselective HDA reactions with ketones, albeit with modest ee: M. Quimpére and K. Jankowski, J. Chem. Soc., Chem. Commun., 1987, 676. See also P. C. B. Page, P. H. Williams, E. W. Collington and H. Finch, J. Chem. Soc., Chem. Commun., 1987, 756.