Highly diastereoselective addition of the lithium enolate of α-diazoacetoacetate to N-sulfinyl imines: Enantioselective synthesis of 2-oxo and 3-oxo pyrrolidines

Journal of Organic Chemistry

Volumn 73, Issue 5, 2008, Pages 1971-1974

  Dong, Changqing ^a   Mo, Fanyang ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM ENOLATE; WOLFF REARRANGEMENT;

CATALYST ACTIVITY; ENANTIOSELECTIVITY; RHODIUM; SYNTHESIS (CHEMICAL);

LITHIUM COMPOUNDS;

2 OXO PYRROLIDINE; 3 OXO PYRROLIDINE; LITHIUM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

ACETATES; IMINES; LITHIUM; MODELS, MOLECULAR; PYRROLIDINES; STEREOISOMERISM;

EID: 41149136851     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702275a     Document Type: Article

References (64)

1. For selected reviews, see: (a) Daly, J. W.; Spande, T. F.; Garraffo, H. M. J. Nat. Prod. 2005, 68, 1556-1575.
2. (b) O' Hagan, D. Nat. Prod. Rep. 2000, 17, 435-442.
3. (c) Leclercq, S.; Braekman, J. C.; Daloze, D.; Pasteels, J. M. Prog. Chem. Org. Nat. Prod. 2000, 79, 115-229.
4. (d) Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1-10.
5. For recent reviews on 2-oxo pyrrolidine syntheses, see: (a) Huang, P.-Q. In New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles; Research Signpost: Trivandrum, India, 2005; pp 197-222.
6. (b) Smith, M. B. In Science of Synthesis; Weinreb, S., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 2005; Vol 21, pp 647-711.
7. (c) Renaud, P.; Giraud, L. Synthesis 1996, 913-926.
8. (d) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543-17594.
9. (e) Ley, S. V.; Cox, L. R.; Meek, G. Chem. Rev. 1996, 96, 423-442.
10. For recent examples of the synthesis of 2-oxo pyrrolidines through ring expansions, see: (a) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993-996.
11. (b) Park, J.-H.; Ha, J.-R.; Oh, S.-J.; Kim, J.-A.; Shin, D.-S.; Won, T.-J.; Lam, Y.-F.; Ahn, C. Tetrahedron Lett. 2005, 46, 1755-1757.
12. (c) Alcaide, B.; Almendros, P.; Cabrero, G.; Ruiz, M. P. Org. Lett. 2005, 7, 3981-3984.
13. (d) Van Brabandt, W.; De Kimpe, N. J. Org. Chem. 2005, 70, 3369-3374.
14. (e) Scott, M. E.; Schwarz, C. A.; Lautens, M. Org. Lett. 2006, 8, 5521-5524.
15. For examples of [3 + 2] annulations in 2-oxo pyrrolidine synthesis, see: (a) Roberson, C. W.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1434-1435.
16. (b) Sun, P.-P.; Chang, M.-Y.; Chiang, M. Y.; Chang, N.-C. Org. Lett. 2003, 5, 1761-1763.
17. (c) Romero, A.; Woerpel, K. A. Org. Lett. 2006, 8, 2127-2130.
18. For recent examples of 2-oxo pyrrolidine synthesis by metal carbene intramolecular C-H insertions, see: (a) Yoon, C. H.; Zaworotko, M. J.; Moulton, B.; Jung, K. W. Org. Lett. 2001, 3, 3539-3542.
19. (b) Wee, A. G. H.; Duncan, S. C. Tetrahedron Lett. 2002, 43, 6173-6179.
20. (c) Yoon, C. H.; Nagle, A.; Chen, C.; Gandhi, D.; Jung, K. W. Org. Lett. 2003, 5, 2259-2262.
21. (d) Choi, M. K.-W.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2005, 7, 1081-1084.
22. (e) Wee, A. G. H.; Duncan, S. C.; Fan, G. J. Tetrahedron: Asymmetry 2006, 17, 297-307.
23. For recent examples of other methods to synthesize 2-oxo pyrrolidines, see: (a) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838-5839.
24. (b) Benati, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S.; Zanardi, G. Org. Lett. 2002, 4, 3079-3081.
25. (c) Vergnon, A. L.; Pottorf, R. S.; Winters, M. P.; Player, M. R. J. Comb. Chem. 2004, 6, 903-910.
26. (d) Hu, T.; Li, C. Org. Lett. 2005, 7, 2035-2038.
27. (e) He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131-3134.
28. (f) Ramachandran, P. V.; Burghardt, T. E. Chem. Eur. J. 2005, 11, 4387-4395.
29. (g) Masse, C. E.; Ng, P. Y.; Fukase, Y.; Sanchez-Rosello, M.; Shaw, J. T. J. Comb. Chem. 2006, 8, 293-296.
30. (h) Gheorghe, A.; Schulte, M.; Reiser, O. J. Org. Chem. 2006, 71, 2173-2176.
31. (i) Zhou, C.-Y.; Che, C.-M. J. Am. Chem. Soc. 2007, 129, 5828-5829.
32. For intramolecular N-H bond insertion in the synthesis of 3-oxo pyrrolidine derivatives, see: (a) Moyer, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223-5230.
33. (b) Clark, J. S.; Hodgson, P. B. J. Chem. Soc., Chem. Commun. 1994, 2701-2702.
34. (c) Wang, J.; Hou, Y.; Wu, P. J. Chem. Soc., Perkin Trans. 1 1999, 2277-2280.
35. (d) Yang, H.; Jurkauskas, V.; Mackintosh, N.; Mogren, T.; Stephenson, C. R. J.; Foster, K.; Brown, W.; Roberts, E. Can. J. Chem. 2000, 78, 800-808.
36. (e) Davis, F. A.; Fang, F.; Goswami, R. Org. Lett. 2002, 4, 1599-1602.
37. Berlin, S.; Ericsson, C.; Engman, L. J. Org. Chem. 2003, 68, 8386-8396.
38. For recent examples of enantioselective synthesis of 2-oxo and 3-oxo pyrrolidines, see: (a) Escalante, J.; González-Tototzin, M. A. Tetrahedron: Asymmetry 2003, 14, 981-985.
39. (b) Fernandes, R. A.; Yamamoto, Y. J. Org. Chem. 2004, 69, 3562-3564.
40. (c) Newhouse, B.; Allen, S.; Fauber, B.; Anderson, A. S.; Eary, C. T.; Hansen, J. D.; Schiro, J.; Gaudino, J. J.; Laird, E.; Chantry, D.; Eberhardt, C.; Burgess, L. E. Bioorg. Med. Chem. Lett. 2004, 14, 5537-5542.
41. (d) Forzato, C.; Nitti, G.; Pitacco, E.; Valentin, S.; Morganti, E.; Rizzato, D.; Spinelli, C.; Dell'Erba, P.; Petrillo, G.; Tavani, C. Tetrahedron 2004, 60, 11011-11027.
42. (e) Ramachandran, P. V.; Burghardt, T. E. Chem. Eur. J. 2005, 11, 4387-4395.
43. (f) Park, J.-H.; Ha, J.-R.; Oh, S.-J.; Kim, J.-A.; Shin, D.-S.; Won, T.-J.; Lam, Y.-F.; Ahn, C. Tetrahedron Lett. 2005, 46, 1755-1757.
44. (g) Raghavan, B.; Johnson, R. L. J. Org. Chem. 2006, 71, 2151-2154.
45. (h) Hansen, J. D.; Newhouse, B. J.; Allen, S.; Anderson, A.; Eary, T.; Schiro, J.; Gaudino, J.; Laird, E.; Allen, A. C.; Chantry, D.; Eberhardt, C.; Burgess, L. E. Tetrahedron Lett. 2006, 47, 69-72.
46. (i) Davis, F. A.; Xu, H.; Wu, Y.; Zhang, J. Org. Lett. 2006, 8, 2273-2276.
47. (a) Deng, G.; Jiang, N.; Ma, Z.; Wang, J. Synlett 2002, 1913-1915.
48. (b) Dong, C.; Deng, G.; Wang, J. J. Org. Chem. 2006, 71, 5560-5564.
49. (a) Calter, M. A.; Sugathapala, P. M.; Zhu, C. Tetrahedron Lett. 1997, 38, 3837-3840.
50. (b) Calter, M. A.; Zhu, C. J. Org. Chem. 1999, 64, 1415-1419.
51. (c) Deng, G.; Tian, X.; Qu, Z.; Wang, J. Angew. Chem., Int. Ed. 2002, 41, 2773-2776.
52. (d) Zhao, Y.; Wang, J. Synlett 2005, 2886-2892.
53. (e) Liao, M.; Dong, S.; Deng, G.; Wang, J. Tetrahedron Lett. 2006, 47, 3927-3929.
54. For reviews, see: (a) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
55. (b) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003-8030.
56. (a) Kundu, K.; Doyle, M. P. Tetrahedron: Asymmetry 2003, 17, 574-577.
57. (b) Doyle, M. P.; Kundu, K.; Russell, A. E. Org. Lett. 2005, 7, 3131-3134.
58. (a) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60, 7037-7039.
59. (b) Davis, F. A.; Yang, B. J. Am. Chem. Soc. 2005, 127, 8398-8407.
60. For a recent review on Wolff rearrangement, see: Kirmse, W. Eur. J. Org. Chem. 2002, 2193-2256.
61. (a) Wang, J.; Hou, Y. J. Chem. Soc. Perkin Trans. 1 1998, 1919-1924.
62. (b) Wang, J.; Hou, Y.; Wu, P.; Qu, Z.; Chan, A. S. C. Tetrahedron: Asymmetry 1999, 10, 4553-4561.
63. (c) Lee, D. J.; Kim, K.; Park, Y. J. Org. Lett. 2002, 4, 873-876.
64. Jeffrey, P. D.; McCombie, S. W. J. Org. Chem. 1982, 47, 587-590.