Enantioselective synthesis of cis-4-formyl-β-lactams via chiral N-heterocyclic carbene-catalyzed kinetic resolution

Advanced Synthesis and Catalysis

Volumn 350, Issue 9, 2008, Pages 1258-1262

  Li, Gong Qiang ^a   Li, Yi ^a   Dai, Li Xin ^a   You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

4 formyl lactams; Asymmetric catalysis; Kinetic resolution; N heterocyclic carbene; Organocatalysis

Indexed keywords

EID: 53849146359     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800071     Document Type: Article

References (71)

1. For reviews on β-lactam antibiotics, see: a) W. Dürckheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew. Chem. 1985, 97, 183-205;
2. Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202;
3. b) Chemistry and Biology of β-Lactam Antibiotics, (Eds.: R. B. Morin, M. Gorman), Academic Press, New York, 1982; Vols. 1-3;
4. c) The Chemistry of β-Lactams, (Eds.: M. I. Page), Chapman and Hall, London, 1992;
5. d) S. Coulton, E. Hunt, Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, (Ed.: G. Lukacs), Springer, Berlin, 1993, Vol. 2, p 621;
6. e) R. Southgate, Contemp. Org. Synth. 1994, 1, 417-431.
7. a) T. Nagahara, T. Kametani, Heterocycles 1987, 25, 729-806;
8. b) R. C. Thomas, in: Recent Progress in the Chemical Synthesis of Antibiotics, (Eds.: G. Lukacs, M. Ohno), Springer-Verlag, Berlin, 1990, p 553;
9. c) C. Palomo, in: Recent Progress in the Chemical Synthesis of Antibiotics, (Eds.: G. Lukacs, M. Ohno), Springer-Verlag, Berlin, 1990, p 565;
10. d) B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Rev. 2007, 107, 4437-4492;
11. e) É. Boros, F. Bertha, G. Czira, A. Feller, J. Fetter, M. Kajtár-Peredy, G. Simig, J. Heterocycl. Chem. 2006, 43, 371-388;
12. f) A. S. Kale, V. G. Puranik, A. R. A. S. Deshmukh, Synthesis 2007, 1159-1164;
13. g) A. S. Kale, P. S. Sakle, V. K. Gumaste, A. R. A. S. Deshmukh, Synthesis 2007, 2631-2636.
14. For reviews: a) G. A. Koppel, Small Ring Heterocycles, (Ed.: A. Hasner), Wiley, New York, 1983; Vol. 42, p 219;
15. b) B. Alcaide, P. Almendros, Chem. Soc. Rev. 2001, 30, 226-240;
16. c) B. Alcaide, P. Almendros, Curr. Org. Chem. 2002, 6, 245-264;
17. for recent examples, see: d) B. Alcaide, P. Almendros, J. M. Alonso, M. F. Aly, Chem. Eur. J. 2003, 9, 3415-3426;
18. e) G. Subramaniyan, R. Raghunathan, A. M. Martin Castro, Tetrahedron 2003, 59, 335-340;
19. f) B. Alcaide, P. Almendros, M. C. Redondo, Org. Lett. 2004, 6, 1765-1767;
20. g) B. Alcaide, P. Almendros, J. M. Alonso, J. Org. Chem. 2004, 69, 993-996;
21. h) B. Alcaide, P. Almendros, G. Cabrero, M. P. Ruiz, Org. Lett. 2005, 7, 3981-3984;
22. i) N. Arumugam, J. Jayashankaran, R. D. R. S. Manian, R. Raghunathan, Tetrahedron 2005, 61, 8512-8516;
23. j) B. Alcaide, P. Almendros, R. Rodríguez-Acebes, J. Org. Chem. 2005, 70, 2713-2719;
24. k) B. Alcaide, P. Almendros, M. C. Redondo, M. P. Ruiz, J. Org. Chem. 2005, 70, 8890-8894;
25. l) B. Alcaide, P. Almendros, A. Luna, M. R. Torres, J. Org. Chem. 2006, 71, 4818-4822;
26. m) B. Alcaide, P. Almendros, C. Aragoncillo, M. C. Redondo, M. R. Torres, Chem. Eur. J. 2006, 12, 1539-1546.
27. a) H. Staudinger, Justus Liebigs Ann. Chem. 1907, 356, 51-123;
28. b) T. T. Tidwell, Angew. Chem. 2008, 120, 1032-1036;
29. Angew. Chem. Int. Ed. 2008, 47, 1016-1020.
30. For reviews on the asymmetric Staudinger reaction, see: a) R. D. G. Cooper, B. W. Daugherty, D. B. Boyd, Pure Appl. Chem. 1987, 59, 485-492;
31. b) F. H. Van der Steen, G. Van Koten, Tetrahedron 1991, 47, 7503-7524;
32. c) C. Polomo, J. M. Aizpurua, I. Ganboa, M. Oiarbide, Eur. J. Org. Chem. 1999, 3223-3235;
33. d) S. France, A. Weatherwax, A. E. Taggi, T. Lectka Acc. Chem. Res. 2004, 37, 592-600;
34. e) G. C. Fu Acc. Chem. Res. 2004, 37, 542-547;
35. selected recent examples: f) E. C. Lee, B. L. Hodous, E. Bergin, C. Shih, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 11586-11587;
36. g) Y.-R. Zhang, L. He, X. Wu, P.-L. Shao, S. Ye, Org. Lett. 2008, 10, 277-280.
37. a) C. Palomo, F. P. Cossio, C. Cuevas, B. Lecea, A. Mielgo, P. Román, A. Luque, M. Martinez-Ripoll, J. Am. Chem. Soc. 1992, 114, 9360-9369;
38. b) R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, F. Ponzini, J. Org. Chem. 1993, 58, 4746-4748;
39. c) M. Jayaraman, A. R. S. Deshmukh, B. M. Bhawal, J. Org. Chem. 1994, 59, 932-934;
40. d) A. Macías, E. Alonso, C. D. Pozo, A. Venturini, J. González, J. Org. Chem. 2004, 69, 7004-7012;
41. e) M. Laurent, M. Cérésiat, J. Marchand-Brynaert, Eur. J. Org. Chem. 2006, 3755-3766;
42. f) W. V. Brabandt, M. Vanwalleghem, M. D'hooghe, N. D. Kimpe, J. Org. Chem. 2006, 71, 7083-7086.
43. a) B. T. Grobel, D. Seebach, Synthesis 1977, 357-402;
44. b) D. Seebach, Angew. Chem. 1979, 91, 259-278;
45. Angew. Chem. Int. Ed. Engl. 1979, 18, 239-258.
46. For reviews on stable carbenes as organocatalysts: a) D. Enders, T. Balensiefer, Acc. Chem. Res. 2004, 37, 534-541;
47. b) J. S. Johnson, Angew. Chem. 2004, 116, 1348-1350;
48. Angew. Chem. Int. Ed. 2004, 43, 1326-1328;
49. c) V. Nair, S. Bindu, V. Sreekumar, Angew. Chem. 2004, 116, 5240-5245;
50. Angew. Chem. Int. Ed. 2004, 43, 5130-5135;
51. d) M. Christmann, Angew. Chem. 2005, 117, 2688-2690;
52. Angew. Chem. Int. Ed. 2005, 44, 2632-2634;
53. e) K. Zeitler, Angew. Chem. 2005, 117, 7674-7678;
54. Angew. Chem. Int. Ed. 2005, 44, 7506-7510;
55. f) N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007, 119, 3046-3058;
56. Angew. Chem. Int. Ed. 2007, 46, 2988-3000;
57. g) D. Enders, O. Niemeier, A. Hwnseler, Chem. Rev. 2007, 107, 5606-5655.
58. For recent examples of NHC as organocatalysts: a) L. He, T.-Y. Jian, S. Ye, J. Org. Chem. 2007, 72, 7466-7468;
59. b) J. J. Song, Z. Tan, J. T. Reeves, N. K. Yee, C. H. Senanayake, Org. Lett. 2007, 9, 1013-1016;
60. c) H. Takikawa, K. Suzuki, Org. Lett. 2007, 9, 2713-2716;
61. d) G.-Q. Li, L.-X. Dai, S.-L. You, Chem. Commun. 2007, 852-854;
62. e) P.-C. Chiang, J. Kaeobamrung, J. W. Bode, J. Am. Chem. Soc. 2007, 129, 3520-3521;
63. f) A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 5334-5335;
64. g) W. Jeong, J. L. Hedrick, R. Waymouth, J. Am. Chem. Soc. 2007, 129, 8414-8415;
65. h) M. Wadamoto, E. M. Phillips, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 10098-10099;
66. i) H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796-13797;
67. j) J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798-13799;
68. k) M. He, J. W. Bode, J. Am. Chem. Soc. 2008, 130, 418-419.
69. a) G.-Q. Li, Y. Li, L.-X. Dai, S.-L. You, Org. Lett. 2007, 9, 3519-3521;
70. for an excellent independent work, see: b) B. Alcaide, P. Almendros, G. Cabrero, M. P. Ruiz, Chem. Commun. 2007, 4788-4790.
71. CCDC 676219 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.