Chiral N-heterocyclic carbene catalyzed staudinger reaction of ketenes with imines: Highly enantioselective synthesis of N-boc β-lactams

Organic Letters

Volumn 10, Issue 2, 2008, Pages 277-280

  Zhang, Yan Rong ^a   He, Lin ^a   Wu, Xu ^a   Shao, Pan Lin ^a   Ye, Song ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; ETHYLENE DERIVATIVE; IMINE; KETENE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BETA-LACTAMS; CATALYSIS; ETHYLENES; IMINES; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 38749111840     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702759b     Document Type: Article

References (74)

1. (a) Igau, A.; Grützmaxher, H.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc. 1988, 110, 6463.
2. (b) Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
3. (c) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
4. (a) Hahn, F. E. Angew. Chem., Int. Ed. 2006 45, 1348.
5. (b) Cheng, Y.; Meth-Cohn, O. Chem. Rev. 2004, 104, 2507.
6. (c) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
7. (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
8. (a) N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry, Vol. 28; Springer-Verlag: Berlin/Heidelberg, 2007.
9. (b) N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
10. (c) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
11. For reviews, see: (a) Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
12. (b) Zeitler, K. Angew. Chem., Int. Ed. 2005, 44, 7506.
13. (c) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
14. (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
15. (b) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem., Int. Ed. 2006, 45, 1463.
16. (c) Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Angew. Chem., Int. Ed. 2006, 45, 3492.
17. (d) Li, G. Q.; Dai, L. X.; You, S. L. Chem. Commun. 2007, 852.
18. (e) Kerr, M. S.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 1029.
19. (f) Liu, Q.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2552.
20. (a) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205.
21. (b) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
22. (c) Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736.
23. (d) Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334.
24. (e) Chiang, P. C.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520.
25. (f) Phillips, E. M.; Wadamoto, M.; Chan, A.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 3107.
26. (g) Wadamoto, M.; Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 10098.
27. (a) Reynolds, N. T.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518.
28. (b) He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088.
29. Chow, K. Y. K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126.
30. Sohn, S. S.; Bode, J. W. Angew. Chem., Int. Ed. 2006, 45, 6021.
31. Li, G.-Q.; Li, Y.; Dai, L.-X.; You, S.-L. Org. Lett. 2007, 9, 3519.
32. (a) Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hedrick, J. L. J. Am. Chem. Soc. 2001, 124, 914.
33. (b) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583.
34. (c) Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587.
35. (d) Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770.
36. (e) Movassaghi, M.; Schmidt, M. A. Org. Lett. 2005, 7, 2453.
37. (f) Song, J. J.; Tan, Z.; Refes, J. T.; Gallou, F.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2005, 7, 2193.
38. (g) Wu, J.; Sun, X.; Ye, S.; Sun, W. Tetrahedron Lett. 2006, 47, 4813.
39. (h) Thomson, J. E.; Rix, K.; Smith, A. D. Org. Lett. 2006, 8, 3785.
40. (a) Tidwell, T. T. Ketenes, 2nd ed.; John Wiley & Sons: Hoboken, NJ, 2006.
41. (b) Tidwell, T. T. Angew. Chem., Int. Ed. 2005, 44, 5778.
42. (c) Orr, R. K.; Calter, M. A. Tetrahedron 2003, 59, 3545.
43. He, L.; Jian, T.-Y.; Ye, S. J. Org. Chem. 2007, 72, 7466.
44. For the biological activity of β-lactams, see: (a) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3.
45. (b) Burnett, D. A. Curr. Med. Chem. 2004, 11, 1873.
46. (c) Buynak, J. D. Curr. Med. Chem. 2004, 11, 1951.
47. (d) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333.
48. For the synthesis and application of β-lactams, see: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437.
49. (b) Dhawan, R.; Dghaym, R. D.; Syr, D. J.; Arndtsen, B. A. Org. Lett. 2006, 8, 3927.
50. (c) Zhao, L.; Li, C.-J. Chem. Asian J. 2006, 1, 203.
51. (d) Ye, M.-C.; Zhou, J.; Tang, Y. J. Org. Chem. 2006, 71, 3576.
52. (e) Shintani, R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 4082.
53. (f) Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572.
54. (a) Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51.
55. (b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Curr. Med. Chem. 2004, 11, 1837.
56. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223.
57. (d) Jiao, L.; Liang, Y.; Xu, J. J. Am. Chem. Soc. 2006, 128, 6060.
58. (a) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831.
59. (b) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D. F.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626.
60. (c) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206.
61. (d) France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592.
62. (a) Lee, E. C.; Hodous, B. L.; Bergin, E.; Shih, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 11586.
63. (b) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
64. (c) Fu, G. C. Acc. Chem. Res. 2004, 37, 542.
65. Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R. Tetrahedron 1999, 55, 14523.
66. (a) Kerr, M. S.; De Alaniz, J. R.; Rovis, T. J. Org. Chem. 2005, 70, 5725.
67. (b) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem., Int. Ed. 2006, 45, 1463.
68. (c) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1998, 1891.
69. He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131.
70. It was found that NHC 8b′ could react with N-tosyl imines, but we were unable to identify or isolate the corresponding NHC-imine adduct.
71. Baldwin, J. E.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1977, 233.
72. (a) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353.
73. (b) Ostendorf, M.; Dijkink, J.; Rutjes, F. P. J. T.; Hiemstra, H. Eur. J. Org. Chem. 2000, 115.
74. Scaling up the reaction from 0.51 mmol (imine 2h) to 8.6 mmol made no notable difference in yield and selectivity.