Enantioselective conjugate addition of hydroxylamines to pyrazolidinone acrylamides

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4181-4184

  Sibi, Mukund P ^a   Liu, Mei ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001218250     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016807t     Document Type: Article

References (47)

1. (a) Catalytic Asymmetric Synthesis, Ojima, I. Ed.; Wiley-VCH: New York; 2000.
2. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; 1999.
3. For examples of chiral relay in diastereoselective transformations, see; (a) Bull. S. D.; Davies, S. G.; Fox, D. J.; Garner, A. C.; Sellers, T. G. R. Pure Appl. Chem. 1998, 70, 1501.
4. (b) Bull, S. D.; Davies. S. G.; Epstein, S. W.; Ouzman, J. V. A. J. Chem. Soc. Chem. Commun. 1998, 659.
5. (c) Bull, S. D.; Davies, S. G.; Epstein, S. W.; Leech, M. A.; Ouzman, J. V. A. J. Chem. Soc., Perkin Trans, 1 1998, 2321.
6. Examples of chiral relay in enantioselective transformations: (a) Watanabe, Y.; Mase, N.; Furue, R.; Toru, T. Tetrahedron Lett. 2001, 42, 2981.
7. (b) Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161.
8. (c) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802.
9. (d) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
10. (e) Hiroi, K.; Ishii, M. Tetrahedron Lett. 2000, 41, 7071.
11. (f) Quaranta, L.; Ph. D thesis, University of Fribourg, Switzerland, 2000.
12. (g) Quaranta, L.; Renaud, P. Chimia 1999, 53, 364.
13. (h) Wada, E.; Pei, W.; Kanemasa, S. Chem. Lett. 1994, 2345.
14. (i) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637.
15. Sibi, M. P.; Venkatraman, L.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc 2001, 123, 8444.
16. For a review see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. For other reviews in the area, see: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. Tomioka, K. In Modern Carbonyl Chemistry, Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; pp 491. Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051.
17. For a review see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. For other reviews in the area, see: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. Tomioka, K. In Modern Carbonyl Chemistry, Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; pp 491. Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051.
18. For a review see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. For other reviews in the area, see: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. Tomioka, K. In Modern Carbonyl Chemistry, Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; pp 491. Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051.
19. For a review see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. For other reviews in the area, see: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171. Tomioka, K. In Modern Carbonyl Chemistry, Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; pp 491. Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051.
20. For work from our laboratory, see (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.
21. (b) Sibi, M. P.; Liu, M. Org, Lett. 2000, 2, 3393. For work from other laboratories see:
22. (c) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28. 179.
23. (d) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291.
24. (e) Ishikawa, T.; Nagai, K.; Senzaki, M.; Tatsukawa, A.; Saito, S. Tetrahedron 1998, 54, 2433.
25. (f) Baldwin, J. E.; Harwood: L. M.; Lombard, M. J. Tetrahedron 1984, 40, 4363.
26. (g) Stamm, H.; Steudle, H. Tetrahedron Lett. 1976, 3607.
27. (h) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 3945.
28. (i) Keen, S. P.; Weinreb, S. M. Tetrahedron Lett. 2000, 41, 4307.
29. (j) Socha, D.; Jurczak, M.; Chmielewski, M. Tetrahedron 1997, 53, 739.
30. (k) Niu, D.; Zhao, K. J. Am. Chem. Soc. 1999, 121, 2456.
31. gem-Dialkyl substitution has been effectively used to control retainers in the design of chiral auxiliaries. For relevant contributions, see: Onimura, K.; Kanemasa, S. Tetrahedron 1992, 48, 8631.
32. (a) Bull, S. D.; Davies, S. G.; Hones, S.; Sanganee, H. J. J. Chem. Soc., Perkin Trans. 1 1999, 387.
33. (b) Bull, S. D.; Davies, S. G.; Key, M-S.; Nicholson, R. L.; Savory, E. D. Chem. Commun. 2000, 1721.
34. Only 29% ee was obtained with pyrrolidinone crotonate (nonrelay substrate) in i-Pr-box ligand catalyzed conjugate addition of p-methoxy-benzyl hydroxylamine.
35. Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C; Trere, A. J. Org. Chem. 1993, 58, 5615.
36. For a review on reversal of stereochemistry, see: Sibi, M. P.; Liu, M. Curr. Org. Chem. 2001, 5, 719.
37. (a) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879.
38. (b) Sibi, P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200.
39. Reasons for the high selectivity in this case are not clear at the present time. It may reflect a different chelation with N(1) nitrogen and the Lewis acid.
40. (12)Penta- and hexacoordinated zinc complexes are well-known and used for understanding reaction mechanisms of zinc enzymes: (a) Bock, C. W.; Katz, A. K.; Glusker, J. P. J. Am. Chem. Soc. 1995, 117, 3754.
41. (b) Bhattacharya, S.; Kumar, S. B.; Dutta, S. K.; Tiekink, E. T. T.; Chaudhury. M. Inorg. Chem. 1996, 55, 1967.
42. For issues related to metal geometry in chiral Lewis acid catalysis, see: (a) ref 10.
43. (b) Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955.
44. (c) Porter, N. A.; Feng, H.; Kavrakova, I. K. Tetrahedron Lett. 1999, 40, 6713.
45. (d) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299.
46. (e) Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481.
47. (f) Yao, S.; Johannsen, M.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans, 1 1997, 2345.