Enantioselective synthesis of substituted pyrrolidines by dynamic resolution

Angewandte Chemie - International Edition

Volumn 41, Issue 20, 2002, Pages 3887-3889

  Coldham, Iain ^a   Dufour, Samuel ^a   Haxell, Thomas F N ^a   Howard, Steven ^b   Vennall, Graham P ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Amines; Carbanions; Dynamic resolution; Enantioselectivity; Lithiation

Indexed keywords

ADDITION REACTIONS; DERIVATIVES; LITHIUM COMPOUNDS;

LIGANDS;

ORGANOMETALLICS;

ALLYL COMPOUND; BENZYL DERIVATIVE; LITHIUM DERIVATIVE; ORGANOLITHIUM COMPOUND; PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0037131505     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021018)41:20<3887::AID-ANIE3887>3.0.CO;2-J     Document Type: Article

References (45)

1. For a review, see A. Basu, S. Thayumanavan, Angew. Chem. 2002, 114, 740-763; Angew. Chem. Int. Ed. 2002, 41, 716-738.
2. For a review, see A. Basu, S. Thayumanavan, Angew. Chem. 2002, 114, 740-763; Angew. Chem. Int. Ed. 2002, 41, 716-738.
3. a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316;
4. a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316;
5. b) P. Beak, A. Basu, D. J. Gallagher, Y. S. Park, S. Thayumanavan, Acc. Chem. Res. 1996, 29, 552-560.
6. a) P. Beak, D. R. Anderson, M. D. Curtis, J. M. Laumer, D. J. Pippel, G. A. Weisenburger, Acc. Chem. Res. 2000, 33, 715-727;
7. b) S. Caddick, K. Jenkins, Chem. Soc. Rev. 1996, 447-456.
8. a) D. J. Gallagher, H. Du, S. A. Long, P. Beak, J. Am. Chem. Soc. 1996, 118, 11391-11398;
9. b) S. Thayumanavan, A. Basu, P. Beak, J. Am. Chem. Soc. 1997, 119, 8209-8216;
10. c) X. Wei, R.J.K. Taylor, Tetrahedron: Asymmetry 1997, 8, 665-668;
11. d) X. Li, L. B. Schenkel, M. C. Kozlowski, Org. Lett. 2000, 2, 875-878;
12. e) V. Derdau, V. Snieckus, J. Org. Chem. 2001, 66, 1992-1998;
13. f) T. Kimachi, Y. Takemoto, J. Org. Chem. 2001, 66, 2700-2704.
14. a) M. Schlosser, D. Limat, J. Am. Chem. Soc. 1995, 117, 12342-12343;
15. b) G. A. Weisenburger, N. C. Faibish, D.J. Pippel, P. Beak, J. Am. Chem. Soc. 1999, 121, 9522-9530.
16. a) O. Zschage, D. Hoppe, Tetrahedron 1992, 48, 5657-5666;
17. b) K. Behrens, R. Fröhlich, O. Meyer, D. Hoppe, Eur. J. Org. Chem. 1998, 2397-2403;
18. c) M. Özlügedik, J. Kristensen, B. Wibbeling, R. Fröhlich, D. Hoppe, Eur. J. Org. Chem. 2002, 414-427;
19. d) N. Komine, L.-F. Wang, K. Tomooka, T. Nakai, Tetrahedron Lett. 1999, 40, 6809-6812;
20. e) K. Tomooka, L.-F. Wang, N. Komine, T. Nakai, Tetrahedron Lett. 1999, 40, 6813-6816;
21. f) K. Tomooka, L.-F. Wang, F. Okazaki, T. Nakai, Tetrahedron Lett. 2000, 41, 6121-6125;
22. g) S. Arrasate, E. Lete, N. Sotomayor, Tetrahedron: Asymmetry 2002, 13, 311-316.
23. S. Nakamura, R. Nakagawa, Y. Watanabe, T. Toru, J. Am. Chem. Soc. 2000, 122, 11340-11347; S. Nakamura, A. Furutani, T. Toru, Eur J. Org. Chem. 2002, 1690-1695.
24. S. Nakamura, R. Nakagawa, Y. Watanabe, T. Toru, J. Am. Chem. Soc. 2000, 122, 11340-11347; S. Nakamura, A. Furutani, T. Toru, Eur J. Org. Chem. 2002, 1690-1695.
25. a) B. Kaiser, D. Hoppe, Angew. Chem. 1995, 107, 344-346; Angew. Chem. Int. Ed. Engl. 1995, 34, 323-325;
26. a) B. Kaiser, D. Hoppe, Angew. Chem. 1995, 107, 344-346; Angew. Chem. Int. Ed. Engl. 1995, 34, 323-325;
27. b) R. W. Hoffmann, W. Klute, R. K. Dress, A. Wenzel, J. Chem. Soc. Perkin Trans. 2 1995, 1721-1726;
28. c) R. W. Hoffmann, W. Klute, Chem. Eur. J. 1996, 2, 694-700.
29. a) H. J. Reich, M. D. Bowe, J. Am. Chem. Soc. 1990, 112, 8994-8995;
30. b) A. Krief, E. Badaoui, W. Dumont, Tetrahedron Lett. 1993, 34, 8517-8520;
31. c) H. J. Reich, K. J. Kulicke, J. Am. Chem. Soc. 1995, 117, 6621-6622;
32. d) H. Ahlbrecht, J. Harbach, R. W. Hoffmann, T. Ruhland, Liebigs Ann. 1995, 211-216;
33. e) R. W. Hoffmann, R. K. Dress, T. Ruhland, A. Wenzel, Chem. Ber. 1995, 128, 861-870;
34. f) G. Fraenkel, J. Cabral, C. Lanter, J. Wang, J. Org. Chem. 1999, 64, 1302-1310;
35. g) O. Stratmann, B. Kaiser, R. Fröhlich, O. Meyer, D. Hoppe, Chem. Eur. J. 2001, 7, 423-435.
36. a) R. E. Gawley, Q. Zhang, J. Org. Chem. 1995, 60, 5763-5769;
37. b) R. E. Gawley, E. Low, Q. Zhang, R. Harris, J. Am. Chem. Soc. 2000, 122, 3344-3350;
38. c) P. Beak, S. T. Kerrick, S. Wu, J. Chu. J. Am. Chem. Soc. 1994, 116, 3231-3239.
39. N. J. Ashweek, I. Coldham, D. J. Snowden, G. P. Vennall, Chem. Eur. J. 2002, 8, 195-207.
40. a) I. Coldham, J.-C. Fernandez, K. N. Price, D. J. Snowden, J. Org. Chem. 2000, 65, 3788-3795;
41. b) I. Coldham. R. Hufton, K. N. Price, R. E. Rathmell, D. J. Snowden, G. P. Vennall, Synthesis 2001, 1523-1531;
42. c) I. Coldham, R. Hufton, D. J. Snowden, J. Am. Chem. Soc. 1996, 118, 5322-5323.
43. N. J. Ashweek, I. Coldham, G. P. Vennall, Tetrahedron Lett. 2000, 41, 2235-2237.
44. A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
45. D. J. Gallagher, S. Wu, N. A. Nikolic, P. Beak, J. Org. Chem. 1995, 60, 8148-8154.