Chiral relay in enantioselective conjugate radical additions using pyrazolidinone templates. How does metal geometry impact selectivity?

Synlett

Volumn , Issue 13, 2004, Pages 2421-2424

  Sibi, Mukund P ^a   Prabagaran, Narayanasamy ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

Chiral Lewis acid; Conjugate additions; Enantioselectivity amplification; Pyrazolidinones; Radical reactions; Relay

Indexed keywords

COPPER; LEWIS ACID; MAGNESIUM; PYRAZOLE DERIVATIVE; PYRAZOLIDINONE; RADICAL; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATE; ENANTIOMER; ENANTIOSELECTIVITY; GEOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 8644242209     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832832     Document Type: Article

References (53)

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 selected examples on the use of achiral templates in enantioselective transformations from other laboratories see: (a) Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559.
4. (b) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1731.
5. (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
6. (d) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559.
7. (e) Jensen, K. B.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471.
8. (f) Kanemasa, S.; Kanai, T. J. Am. Chem. Soc. 2000, 122, 10710.
9. (g) Palomo, C.; Oiarbide, M.; Garcia, J. M.; Gonzalez, A.; Arceo, E. J. Am. Chem. Soc. 2003, 125, 13942.
10. (h) For work from our laboratory see: Sibi, M. P.; Sausker, J. B. J. Am. Chem. Soc. 2002, 124, 984.
11. (i) Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955.
12. (j) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.
13. (k) Sibi, M. P.; Liu, M. Org. Lett. 2000, 2, 3393.
14. Sibi, M. P.; Venkatraman, L.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 2001, 123, 8444.
15. (a) For a mini review on this subject see: Corminboeuf, O.; Quaranta, L.; Renaud, P.; Liu, M.; Jasperse, C. P.; Sibi, M. P. Chem.-Eur. J. 2003, 9, 28.
16. (b) Chiral relay in diastereoselective transformations see: Bull, S. D.; Davies, S. G.; Fox, D. J.; Garner, A. C.; Sellers, T. G. R. Pure Appl. Chem. 1998, 70, 1501.
17. (c) Selected examples of chiral relay in enantioselective transformations: Watanabe, Y.; Mase, N.; Furue, R.; Toru, T. Tetrahedron Lett. 2001, 42, 2981.
18. (d) Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161.
19. (e) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802.
20. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
21. (g) Hiroi, K.; Ishii, M. Tetrahedron Lett. 2000, 41, 7071.
22. (h) Wada, E.; Pei, W.; Kanemasa, S. Chem. Lett. 1994, 2345.
23. (i) Sibi, M. P.; Zhang, R.; Manyem, S. J. Am. Chem. Soc. 2003, 125, 9306.
24. (j) Quaranta, L.; Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 39.
25. (a) Sibi, M. P.; Ma, Z.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 718.
26. (b) Sibi, M. P.; Itoh, K.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 5366.
27. (c) Sibi, M. P.; Liu, M. Org. Lett. 2001, 3, 4181.
28. For reviews on stereoselective radical chemistry see: (a) Renaud, P.; Gèrster, M. Angew. Chem. Int. Ed. 1998, 37, 2563.
29. (b) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
30. (c) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263.
31. (d) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251.
32. (e) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8303.
33. (f) See also: Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
34. (g) Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
35. Enantioselective conjugate radical reactions: (a) Sibi, M. P.; Ji, J.; Wu, J. H.; Gurtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200.
36. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800.
37. (c) Sibi, M. P.; Shay, J. J.; Ji, J. Tetrahedron Lett. 1997, 38, 5955.
38. (d) Sibi, M. P.; Chen, J. J. Am. Chem. Soc. 2001, 123, 9472.
39. (e) Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929.
40. (f) Sibi, M. P.; Petrovic, G. Tetrahedron: Asymmetry 2003, 15, 2879.
41. (g) Sibi, M. P.; Zimmerman, J.; Rheault, T. R. Angew. Chem. Int. Ed. 2003, 42, 4521.
42. (h) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417.
43. (i) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299.
44. (j) Sibi, M. P.; He, L. Org. Lett. 2004, 6, 1749.
45. For the synthesis of pyrazolidinone templates see details in ref.3 and ref.5
46. R minor enantiomer: 14.4 min, major enantiomer: 19.0min).
47. The absolute stereochemistry of the products 5a-d were determined by hydrolysis to the acid and comparison of their rotation with 3-phenyl-4-methyl-pentanoic acid.
48. (a) For a review on stereochemical reversal see: Sibi, M. P.; Liu, M. Curr. Org. Chem. 2000, 5, 735.
49. (b) Evans, D. A.; Johnson, J. S.; Bergey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879.
50. Although the proximity will vary, the ligand will be orthogonal to the substrate so long as one of the ligand nitrogen occupies an apical position, whether that is in an octahedral, trigonal bipyramidal, square pyramidal, or tetrahedral complex.
51. The molecular graphics images in Figure 2 were produced using the UCSF Chimera package from the Computer Graphics Laboratory, University of California-San Francisco.
52. In cycloadditions the bulk of the pyrazolidinone templates can also influence regioselectivity (ref.5b) or exo/endo diastereoselectivity (ref.5a).
53. Magnesium iodide and magnesium triflimide both provide nearly identical results when used in combination with ligand 8; for example see entry 14 in Table 2 and entry 1 in Table 4. The cheaper magnesium iodide was used for experiments in Table 4.