Metal-catalyzed asymmetric hetero-Diels-Alder reactions of unactivated dienes with glyoxylates

Pure and Applied Chemistry

Volumn 70, Issue 5, 1998, Pages 1117-1122

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

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000600431     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199870051117     Document Type: Article

References (23)

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2. See e.g.: (a) D. L. Boger and S. M. Weinreb in Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: New York 1987. (b) H. B. Kagan and O. Riant Chem. Rev., 92, 1008 (1992). (c) H. Waldmann Synthesis, 535 (1994).
3. See e.g.: (a) D. L. Boger and S. M. Weinreb in Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: New York 1987. (b) H. B. Kagan and O. Riant Chem. Rev., 92, 1008 (1992). (c) H. Waldmann Synthesis, 535 (1994).
4. (d) K. Narasaka Synthesis, 1991, 1.
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10. See e.g.: (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy J. Org. Chem. 60, 5998 (1995). (b) M. Quimpére and K. Jankowski J. Chem. Soc., Chem. Commun., 676 (1987). (c) A. Togni Organometallics, 9, 3106 (1990). (d) Y. Motoyama and K. Mikami J. Chem. Soc., Chem. Commun., 1563 (1994). (e) Q. Gao, M. Muruyama, M. Mouri and H Yamamoto J. Org. Chem. 57, 1951 (1992). (f) E. J. Corey, C. L. Cywin and T. D. Roper Tetrahedron Lett., 33, 6907 (1992). (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto J. Am. Chem. Soc., 110, 310 (1988). (f) S. Matsukawa and K. Mikami Tetrahedron: Asymmetry 8, 815 (1997).
11. See e.g.: (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy J. Org. Chem. 60, 5998 (1995). (b) M. Quimpére and K. Jankowski J. Chem. Soc., Chem. Commun., 676 (1987). (c) A. Togni Organometallics, 9, 3106 (1990). (d) Y. Motoyama and K. Mikami J. Chem. Soc., Chem. Commun., 1563 (1994). (e) Q. Gao, M. Muruyama, M. Mouri and H Yamamoto J. Org. Chem. 57, 1951 (1992). (f) E. J. Corey, C. L. Cywin and T. D. Roper Tetrahedron Lett., 33, 6907 (1992). (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto J. Am. Chem. Soc., 110, 310 (1988). (f) S. Matsukawa and K. Mikami Tetrahedron: Asymmetry 8, 815 (1997).
12. See e.g.: (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy J. Org. Chem. 60, 5998 (1995). (b) M. Quimpére and K. Jankowski J. Chem. Soc., Chem. Commun., 676 (1987). (c) A. Togni Organometallics, 9, 3106 (1990). (d) Y. Motoyama and K. Mikami J. Chem. Soc., Chem. Commun., 1563 (1994). (e) Q. Gao, M. Muruyama, M. Mouri and H Yamamoto J. Org. Chem. 57, 1951 (1992). (f) E. J. Corey, C. L. Cywin and T. D. Roper Tetrahedron Lett., 33, 6907 (1992). (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto J. Am. Chem. Soc., 110, 310 (1988). (f) S. Matsukawa and K. Mikami Tetrahedron: Asymmetry 8, 815 (1997).
13. See e.g.: (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy J. Org. Chem. 60, 5998 (1995). (b) M. Quimpére and K. Jankowski J. Chem. Soc., Chem. Commun., 676 (1987). (c) A. Togni Organometallics, 9, 3106 (1990). (d) Y. Motoyama and K. Mikami J. Chem. Soc., Chem. Commun., 1563 (1994). (e) Q. Gao, M. Muruyama, M. Mouri and H Yamamoto J. Org. Chem. 57, 1951 (1992). (f) E. J. Corey, C. L. Cywin and T. D. Roper Tetrahedron Lett., 33, 6907 (1992). (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto J. Am. Chem. Soc., 110, 310 (1988). (f) S. Matsukawa and K. Mikami Tetrahedron: Asymmetry 8, 815 (1997).
14. See e.g.: (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy J. Org. Chem. 60, 5998 (1995). (b) M. Quimpére and K. Jankowski J. Chem. Soc., Chem. Commun., 676 (1987). (c) A. Togni Organometallics, 9, 3106 (1990). (d) Y. Motoyama and K. Mikami J. Chem. Soc., Chem. Commun., 1563 (1994). (e) Q. Gao, M. Muruyama, M. Mouri and H Yamamoto J. Org. Chem. 57, 1951 (1992). (f) E. J. Corey, C. L. Cywin and T. D. Roper Tetrahedron Lett., 33, 6907 (1992). (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto J. Am. Chem. Soc., 110, 310 (1988). (f) S. Matsukawa and K. Mikami Tetrahedron: Asymmetry 8, 815 (1997).
15. See e.g.: (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy J. Org. Chem. 60, 5998 (1995). (b) M. Quimpére and K. Jankowski J. Chem. Soc., Chem. Commun., 676 (1987). (c) A. Togni Organometallics, 9, 3106 (1990). (d) Y. Motoyama and K. Mikami J. Chem. Soc., Chem. Commun., 1563 (1994). (e) Q. Gao, M. Muruyama, M. Mouri and H Yamamoto J. Org. Chem. 57, 1951 (1992). (f) E. J. Corey, C. L. Cywin and T. D. Roper Tetrahedron Lett., 33, 6907 (1992). (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto J. Am. Chem. Soc., 110, 310 (1988). (f) S. Matsukawa and K. Mikami Tetrahedron: Asymmetry 8, 815 (1997).
16. See e.g.: (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy J. Org. Chem. 60, 5998 (1995). (b) M. Quimpére and K. Jankowski J. Chem. Soc., Chem. Commun., 676 (1987). (c) A. Togni Organometallics, 9, 3106 (1990). (d) Y. Motoyama and K. Mikami J. Chem. Soc., Chem. Commun., 1563 (1994). (e) Q. Gao, M. Muruyama, M. Mouri and H Yamamoto J. Org. Chem. 57, 1951 (1992). (f) E. J. Corey, C. L. Cywin and T. D. Roper Tetrahedron Lett., 33, 6907 (1992). (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto J. Am. Chem. Soc., 110, 310 (1988). (f) S. Matsukawa and K. Mikami Tetrahedron: Asymmetry 8, 815 (1997).
17. (a) M. Johannsen and K. A. Jørgensen J. Org. Chem., 60, 5757 (1995).
18. (b) M. Johannsen and K. A. Jørgensen Tetrahedron, 52, 7321 (1996).
19. (c) A. Graven, M. Johannsen and K. A. Jørgensen J. Chem. Soc., Chem. Commun. 2373 (1996).
20. (d) M. Johannsen and K. A. Jørgensen J. Chem. Soc., Perkin Trans. 2 1183 (1997).
21. (e) S. Yao, M. Johannsen and K. A. Jørgensen J. Chem. Soc., Perkin Trans. 1 2345 (1997).
22. S. Yao, M. Johannsen and K. A. Jørgensen submitted for publication.
23. J. R. Rocca, J. H. Tumlinson, B. M. Glancey and C. S. Lofgren Tetrahedron Lett. 1983, 24, 1889.