Catalytic enantioselective aza Diels-Alder reactions of imino dienophiles

Angewandte Chemie - International Edition

Volumn 37, Issue 22, 1998, Pages 3121-3124

  Yao, Sulan ^a   Johannsen, Mogens ^a   Hazell, Rita G ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Asymmetric catalysis; Copper; Cycloadditions; Lewis acids; Synthetic methods

Indexed keywords

ALDEHYDE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY;

EID: 0032484179     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981204)37:22<3121::AID-ANIE3121>3.0.CO;2-J     Document Type: Article

References (39)

1. See for example: a) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press, New York, 1987, chap. 2, 9; b) L. F. Tietze, G. Kettschau, Stereoselective Heterocyclic Synthesis I, Vol. 189 (Ed.: P. Metz), Springer, Berlin, 1997, p. 1; c) H. Waldmann, Synthesis 1994, 535; d) Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, p. 37; e) S. M. Weinreb in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Flemming, M. F. Semmelhack), Pergamon, Oxford, 1991, p. 401.
2. See for example: a) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press, New York, 1987, chap. 2, 9; b) L. F. Tietze, G. Kettschau, Stereoselective Heterocyclic Synthesis I, Vol. 189 (Ed.: P. Metz), Springer, Berlin, 1997, p. 1; c) H. Waldmann, Synthesis 1994, 535; d) Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, p. 37; e) S. M. Weinreb in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Flemming, M. F. Semmelhack), Pergamon, Oxford, 1991, p. 401.
3. See for example: a) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press, New York, 1987, chap. 2, 9; b) L. F. Tietze, G. Kettschau, Stereoselective Heterocyclic Synthesis I, Vol. 189 (Ed.: P. Metz), Springer, Berlin, 1997, p. 1; c) H. Waldmann, Synthesis 1994, 535; d) Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, p. 37; e) S. M. Weinreb in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Flemming, M. F. Semmelhack), Pergamon, Oxford, 1991, p. 401.
4. See for example: a) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press, New York, 1987, chap. 2, 9; b) L. F. Tietze, G. Kettschau, Stereoselective Heterocyclic Synthesis I, Vol. 189 (Ed.: P. Metz), Springer, Berlin, 1997, p. 1; c) H. Waldmann, Synthesis 1994, 535; d) Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, p. 37; e) S. M. Weinreb in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Flemming, M. F. Semmelhack), Pergamon, Oxford, 1991, p. 401.
5. See for example: a) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press, New York, 1987, chap. 2, 9; b) L. F. Tietze, G. Kettschau, Stereoselective Heterocyclic Synthesis I, Vol. 189 (Ed.: P. Metz), Springer, Berlin, 1997, p. 1; c) H. Waldmann, Synthesis 1994, 535; d) Organic Synthesis Highlights II (Ed.: H. Waldmann), VCH, Weinheim, 1995, p. 37; e) S. M. Weinreb in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Flemming, M. F. Semmelhack), Pergamon, Oxford, 1991, p. 401.
6. See for example: a) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310; b) G. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998; c) Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron, 1994, 50, 979; d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951; e) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060, and references therein; f) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403; g) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757; h) A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2372.
7. See for example: a) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310; b) G. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998; c) Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron, 1994, 50, 979; d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951; e) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060, and references therein; f) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403; g) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757; h) A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2372.
8. See for example: a) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310; b) G. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998; c) Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron, 1994, 50, 979; d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951; e) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060, and references therein; f) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403; g) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757; h) A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2372.
9. See for example: a) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310; b) G. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998; c) Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron, 1994, 50, 979; d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951; e) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060, and references therein; f) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403; g) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757; h) A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2372.
10. See for example: a) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310; b) G. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998; c) Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron, 1994, 50, 979; d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951; e) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060, and references therein; f) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403; g) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757; h) A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2372.
11. See for example: a) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310; b) G. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998; c) Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron, 1994, 50, 979; d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951; e) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060, and references therein; f) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403; g) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757; h) A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2372.
12. See for example: a) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310; b) G. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998; c) Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron, 1994, 50, 979; d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951; e) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060, and references therein; f) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403; g) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757; h) A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2372.
13. See for example: a) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310; b) G. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998; c) Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron, 1994, 50, 979; d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951; e) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060, and references therein; f) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403; g) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757; h) A. Graven, M. Johannsen, K. A. Jørgensen, Chem. Commun. 1996, 2372.
14. For reactions with a normal electron demand: a) M. Johannsen, S. Yao, K. A. Jørgensen, Chem. Commun. 1997, 2169;
15. b) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, K. A. Jørgensen, J. Am. Chem. Soc. 1998, 120, 8599.
16. For reactions with an inverse electron demand: a) D. A. Evans, J. S. Johnson, J. Am. Chem. Soc. 1998, 120, 4895;
17. b) J. Thorhauge, M. Johannsen, K. A. Jørgensen, Angew. Chem. 1998, 110, 2543; Angew. Chem. Int. Ed. 1998, 37, 2404.
18. b) J. Thorhauge, M. Johannsen, K. A. Jørgensen, Angew. Chem. 1998, 110, 2543; Angew. Chem. Int. Ed. 1998, 37, 2404.
19. a) K. Hattori, H. Yamamoto, J. Org. Chem. 1992, 57, 3264;
20. b) K. Hattori, H. Yamamoto, Tetrahedron 1993, 49, 1749;
21. c) K. Ishihara, M. Miyata, K. Hattori, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10520.
22. a) H. Ishitani, S. Kobayashi, Tetrahedron Lett. 1996, 37, 7357;
23. b) S. Kobayashi, S. Komiyama, H. Ishitani, Angew. Chem. 1998, 110, 1026; Angew. Chem. Int. Ed. 1998, 37, 979.
24. b) S. Kobayashi, S. Komiyama, H. Ishitani, Angew. Chem. 1998, 110, 1026; Angew. Chem. Int. Ed. 1998, 37, 979.
25. See for example: a) P. Herczegh, I. Kovács, L. Szilágyi, M. Zsély, F. Sztaricskai, A. Berecibar, A. Olesker, G. Lukacs, Tetrahedron Lett. 1992, 33, 3133; b) R. Lock, H. Waldmann, Tetrahedron Lett. 1996, 37, 2753; c) P. N. Devine, M. Reilly, T. Oh, Tetrahedron Lett. 1993, 34, 5827; d) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1445; e) M. M. Midland, R. Koops, J. Org. Chem. 1992, 57, 1158; f) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803.
26. See for example: a) P. Herczegh, I. Kovács, L. Szilágyi, M. Zsély, F. Sztaricskai, A. Berecibar, A. Olesker, G. Lukacs, Tetrahedron Lett. 1992, 33, 3133; b) R. Lock, H. Waldmann, Tetrahedron Lett. 1996, 37, 2753; c) P. N. Devine, M. Reilly, T. Oh, Tetrahedron Lett. 1993, 34, 5827; d) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1445; e) M. M. Midland, R. Koops, J. Org. Chem. 1992, 57, 1158; f) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803.
27. See for example: a) P. Herczegh, I. Kovács, L. Szilágyi, M. Zsély, F. Sztaricskai, A. Berecibar, A. Olesker, G. Lukacs, Tetrahedron Lett. 1992, 33, 3133; b) R. Lock, H. Waldmann, Tetrahedron Lett. 1996, 37, 2753; c) P. N. Devine, M. Reilly, T. Oh, Tetrahedron Lett. 1993, 34, 5827; d) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1445; e) M. M. Midland, R. Koops, J. Org. Chem. 1992, 57, 1158; f) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803.
28. See for example: a) P. Herczegh, I. Kovács, L. Szilágyi, M. Zsély, F. Sztaricskai, A. Berecibar, A. Olesker, G. Lukacs, Tetrahedron Lett. 1992, 33, 3133; b) R. Lock, H. Waldmann, Tetrahedron Lett. 1996, 37, 2753; c) P. N. Devine, M. Reilly, T. Oh, Tetrahedron Lett. 1993, 34, 5827; d) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1445; e) M. M. Midland, R. Koops, J. Org. Chem. 1992, 57, 1158; f) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803.
29. See for example: a) P. Herczegh, I. Kovács, L. Szilágyi, M. Zsély, F. Sztaricskai, A. Berecibar, A. Olesker, G. Lukacs, Tetrahedron Lett. 1992, 33, 3133; b) R. Lock, H. Waldmann, Tetrahedron Lett. 1996, 37, 2753; c) P. N. Devine, M. Reilly, T. Oh, Tetrahedron Lett. 1993, 34, 5827; d) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1445; e) M. M. Midland, R. Koops, J. Org. Chem. 1992, 57, 1158; f) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803.
30. See for example: a) P. Herczegh, I. Kovács, L. Szilágyi, M. Zsély, F. Sztaricskai, A. Berecibar, A. Olesker, G. Lukacs, Tetrahedron Lett. 1992, 33, 3133; b) R. Lock, H. Waldmann, Tetrahedron Lett. 1996, 37, 2753; c) P. N. Devine, M. Reilly, T. Oh, Tetrahedron Lett. 1993, 34, 5827; d) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1445; e) M. M. Midland, R. Koops, J. Org. Chem. 1992, 57, 1158; f) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803.
31. a) D. Ferraris, B. Young, T. Dudding, T. Lectka J. Am. Chem. Soc. 1998, 120, 4548;
32. b) H. Nakamura, K. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 4242;
33. c) E. Hagiwara, A. Fujii, M. Sodeoka, J. Am. Chem. Soc. 1998, 120, 2474.
34. SMART, SAINT, and XPREP: Area Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc. Madison, WI (USA), 1995.
35. G. Cascarano, A. Altomare, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, D. Siliqi, M. C. Burla, G. Polidori, M. Camalli, Acta Crystallogr. Sect. A 1996, 52, C50.
36. a) W. T. Busing, K. O. Martin, H. A. Levy, ORFLS, Report ORNL-TM-305. Oak Ridge National Laboratory, TN (USA), 1962;
37. b) A. Hazell, KRYSTAL, An integrated system of crystallographic programs, Aarhus University (Denmark), 1995.
38. D. Rogers, Acta Crystallogr. Sect. A 1981, 37, 734.
39. M. N. Burnett, C. K. Johnson, ORTEP-III, Report ORNL-6895. Oak Ridge National Laboratory, TN (USA), 1996.