Self-regeneration of stereocenters (SRS) via stereolabile axially chiral intermediates

Topics in Stereochemistry

Volumn 26, Issue , 2010, Pages 53-91

  Carlier, Paul R ^a   Hsu, Danny C ^a   Bryson, Stephanie Antolak ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77958544763     PISSN: 0082500X     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article

References (56)

1. Kawabata, T.; Yahiro, K.; Fuji, K.J. Am. Chem. Soc. 1991, 113, 9694-9696.
2. Braña, M. F.; Garrido, M.; López, M. L.; Sanz, A. M. J. Heterocyclic Chem. 1980, 17, 829.
3. Braña, M. F.; Garrido, M.; López Rodíguez, M. L.; Morcello, M.J. Heterocycles 1987, 26, 2139-2151.
4. Seebach, D.; Wasmuth, D. Angew. Chem. Int. Ed. Engl. 1981, 20, 971.
5. Seebach, D.; Sting, A. R.; Hoffman, M. Angew. Chem. Int. Ed. 1996, 35, 2708-2748.
6. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373-376.
7. Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810.
8. Kawabata, T.; Chen,J.; Suzuki, H.; Nagae, Y.; Kinoshita, T.; Chancharunee, S.; Fuji, K. Org. Lett. 2000, 2, 3883-3885.
9. Zhao, H.; Hsu, D. C.; Carlier, P. R. Synthesis 2005, 1-16.
10. Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994, pp. 1120-1121.
11. Kawabata, T.; Suzuki, H.; Nagae, Y.; Fuji, K. Angew. Chem. Int. Ed. Engl. 2000, 39, 2155-2157.
12. Kawabata, T.; Fuji, K. In Topics in Stereochemistry, Denmark, S. E., Ed. John Wiley & Sons, Inc., New York, 2003, Vol. 23, pp. 175-205.
13. Carlier, P. R.; Zhao, H.; MacQuarrie-Hunter, S. L.; DeGuzman, J. C.; Hsu, D. C. J. Am. Chem. Soc. 2006, 128, 15215-15220.
14. Wolf, C. In Dynamic Stereochemistry of Chiral Compounds: Principles and Applications, Royal Society of Chemistry, Cambridge, UK, 2008, pp. 282-289.
15. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390-5398.
16. Seebach, D.; Fadel, A. Helv. Chim. Acta 1985, 68, 1243-1250.
17. Basu, A.; Thayumanavan, S. Angew. Chem. Int. Ed. 2002, 41, 716-738.
18. Yousaf, T. I.; Williams, R. L.; Coldham, I.; Gawley, R. E. Chem. Commun. 2008, 97-98.
19. Kawabata, T.; Öztürk, O.; Chen, J.; Fuji, K. Chem. Commun. 2003, 162-163.
20. Kramer, W. H.; Griesbeck, A. G. J. Chem. Educ. 2008, 85, 701-709.
21. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624-1654.
22. Espenson, J. H. In Chemical Kinetics and Reaction Mechanisms, 2nd ed., McGraw-Hill, New York, 2002, pp. 46-49.
23. Eyring, H. Chem. Rev. 1935, 17, 65-77.
24. Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds, John Wiley & Sons, New York, 1994, pp. 1142-1148.
25. Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds, John Wiley & Sons, New York, 1994, pp. 597-606.
26. Buckmelter, A. J.; Kim, A. I.; Rychnovsky, S. D.J. Am. Chem. Soc. 2000, 122, 9386-9390.
27. Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuberger, M.; Zehnder, M.; Wessig, P. Angew. Chem. Int. Ed. 1999, 38, 2586-2587.
28. Dalgard, J. E.; Rychnovsky, S. D. Org. Lett. 2004, 6, 2713-2716.
29. Kawabata, T.; Kawakami, S.-p.; Fuji, K. Tetrahedron Lett. 2002, 43, 1465-1467.
30. Kawabata, T.; Kawakami, S.-P.; Shimada, S.; Fuji, K. Tetrahedron 2003, 59, 965-974.
31. Kawabata, T.; Kawakami, S.; Majumdar, S. J. Am. Chem. Soc. 2003, 125, 13012-13013.
32. Kawabata, T.; Chen, J.; Suzuki, H.; Fuji, K. Synthesis 2005, 1368-1377.
33. Kawabata, T.; Matsuda, S.; Kawakami, S.; Monguchi, D.; Moriyama, K. J. Am. Chem. Soc. 2006, 128, 15394-15395.
34. Kawabata, T.; Moriyama, K.; Kawakami, S.; Tsubaki, K. J. Am. Chem. Soc. 2008, 130, 4153-4157.
35. Carlier, P. R.; Lam, P. C.-H.; DeGuzman,J.; Zhao, H. Tetrahedron: Asymmetry 2005, 16, 2998-3002.
36. MacQuarrie-Hunter, S.; Carlier, P. R. Org. Lett. 2005, 7, 5305-5308.
37. Moriyama, K.; Sakai, H.; Kawabata, T. Org. Lett. 2008, 10, 3883-3886.
38. Kawabata, T.; Majumdar, S.; Tsubaki, K.; Monguchi, D. Org. Biomol. Chem. 2005, 3, 1609-1611.
39. Watanabe, T.; Kawabata, T. Heterocycles 2008, 76, 1593-1606.
40. Bonache, M. A.; Cativiela, C.; Garcia-Lopez, M. T.; Gonzalez-Muniz, R. Tetrahedron Lett. 2006, 47, 5883-5887.
41. Bonache, M. A.; Gerona-Navarro, G.; Garcia-Aparicio, C.; Alias, M.; Martin-Martinez, M.; García-López, M. T.; Lopez, P.; Cativiela, C.; Gonzalez-Muniz, R. Tetrahedron: Asymmetry 2003, 14, 2161-2169.
42. Bonache, M. A.; Lopez, P.; Martin-Martinez, M.; Garcia-Lopez, M. T.; Cativiela, C.; Gonza-lez-Muniz, R. Tetrahedron 2006, 62, 130-138.
43. Kolaczkowski, L.; Barnes, D. M. Org. Lett. 2007, 9, 3029-3032.
44. Branca, M.; Gori, D.; Guillot, R.; Alezra, V.; Kouklovsky, C. J. Am. Chem. Soc. 2008, 130, 5864-5865.
45. Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirschfi eld, J. J. Med. Chem. 1988, 31, 2235-2246.
46. Ellman, J. A. Acc. Chem. Res. 1996, 29, 132-143.
47. Carlier, P. R.; Zhao, H.; DeGuzman, J.; Lam, P. C.-H. J. Am. Chem. Soc. 2003, 125, 11482-11483.
48. Linscheid, P.; Lehn, J.-M. Bull. Chim. Soc. Fr. 1967, 992-997.
49. Konowal, A.; Snatzke, G.; Alebic-Kolbah, T.; Kajfez, F.; Rendic, S.; Sunjic, V. Biochem. Pharm. 1979, 28, 3109-3113.
50. Gilman, N. W.; Rosen, P.; Earley, J. V.; Cook, C.; Todaro, L. J. J. Am. Chem. Soc. 1990, 112, 3969-3978.
51. Lam, P. C.-H.; Carlier, P. R. J. Org. Chem. 2005, 70, 1530-1538.
52. Sunjic, V.; Lisini, A.; Sega, A.; Kovac, T.; Kajfez, F.; Ruscic, B. J. Heterocyclic Chem. 1979, 16, 757-761.
53. Dubé, P.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 12062-12063.
54. Griesbeck, A. G.; Kramer, W.; Lex, J. Angew. Chem. Int. Ed. 2001, 40, 577-579.
55. Sakamoto, M.; Kawanishi, H.; Mino, T.; Kasashima, Y.; Fujita, T. Chem. Commun. 2006, 4608-4610.
56. Sakamoto, M.; Kawanishi, H.; Mino, T.; Fujita, T. Chem. Commun. 2008, 2132-2133.