Trisoxazoline/Cu(II)-promoted Kinugasa reaction. Enantioselective synthesis of β-lactams

Journal of Organic Chemistry

Volumn 71, Issue 9, 2006, Pages 3576-3582

  Ye, Meng Chun ^a   Zhou, Jian ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AIR ATMOSPHERE; DIASTEREOSELECTIVITY; ENANTIOSELECTIVE SYNTHESIS; KINUGASA REACTION;

AIR; AMINES; CATALYSTS; ISOMERS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

REACTION KINETICS;

ALKYNE; AMINE; BETA LACTAM; CUPRIC ION; NITRONE; OXAZOLINE DERIVATIVE; TRISOXAZOLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; KINUGUSA REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALKYNES; BETA-LACTAMS; COPPER; LIGANDS; NITROGEN OXIDES; PEPTIDES, CYCLIC; STEREOISOMERISM; TEMPERATURE;

EID: 33646245219     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0602874     Document Type: Article

References (67)

1. (a) Morin, R. B., German, M., Eds.; Chemistry and Biology of β-Lactams Antibiotics; Academic Press: New York, 1982.
2. (b) Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Comprehensive Helerocyclic Chemistry II; Pergamon: New York, 1996; Vol. 1B, Chapters 1.18-1.20.
3. (a) Ojima, I. Acc. Chem. Res. 1995, 28, 383.
4. (b) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377.
5. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Pure Appl. Chem. 2000, 72, 1763.
6. (d) Bruggink, A., Ed.; Synthesis of β-Lactam Antibiotics; Kluwer: Dordrecht, The Netherlands, 2001.
7. For some reviews on employing chiral precursors, see: (a) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 295.
8. (b) Ghosez, L.; Marchand-Brynaert, S. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
9. (c) Hart, D. J.; Ha, D.-C. Chem. Rev. 1989, 89, 1447.
10. For relative reviews, see: (a) Magriotis, P. A. Angew. Chem., Int. Ed. 2001, 40, 4377.
11. (b) France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592.
12. For direct asymmetric catalytic Gilman-Speeter reaction, see: (c) Oilman, H.; Speeter, M. J. Am. Chem. Soc. 1943, 65, 2255.
13. (d) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060.
14. (e) Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. Chem. Commun. 1999, 715.
15. (f) Kambara, T.; Hussein, M. A.; Fujieda, H.; Iida, A.; Tomioka, K. Tetrahedron Lett. 1998, 39, 9055.
16. For direct asymmetric catalytic Staudinger reaction, see: (g) Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51.
17. (h) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831-7832.
18. (i) Wack, H.; Drury, W. J., III; Taggi, A. E.; Ferraris, D.; Lectka, T. Org. Lett. 1999, 1, 1985.
19. (J) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
20. For rhodium-catalyzed carbonylation of an aziridine, see: (k) Calet, S.; Urso, F.; Alper, H. J. Am. Chem. Soc. 1989, 111, 931.
21. For rhodium-catalyzed intramolecular insertion of a α-diazo amide into a C-H bond, see: (l) McCarthy, N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983.
22. (m) Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Daniel, K. L. Tetrahedron Lett. 1992, 33, 7819.
23. (n) Doyle, M. P.; Kalinin, A. V. Synlett 1995, 1075.
24. (o) Watanabe, N.; Anada, M.; Hashimoto, S.-i.; Ikegami, S. Synlett 1994, 1031.
25. (p) Anada, M.; Watanabe, N.; Hashimoto. S.-i. Chem. Commun. 1998, 1517.
26. (q) Anada, M.; Hashimoto, S.-i. Tetrahedron Lett. 1998, 39, 9063. For direct asymmetric catalytic Kinugasa reaction, see ref 5.
27. For a recent review, see: (a) Marco-Contelles, J. Angew. Chem., Int. Ed. 2004, 43, 2198.
28. For the initial report, see: (b) Kinugasa, M.; Hashimoto, S. J. Chem. Soc., Chem. Commun. 1972, 466.
29. For direct asymmetric catalytic versions, see: (c) Miura, M.; Enna, M.; Okuro, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999.
30. (d) Lo, M. M.-C; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572.
31. (e) Shintani, R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 4082.
32. For relative studies and applications, see: (f) Ding, L. K.; Irwin, W. J. J. Chem. Soc., Perkin Trans, 1 1976, 2382.
33. (g) Dutta, D. K.; Boruah, R. C.; Sandhu, J. S. Heterocycles 1986, 24, 655.
34. (h) Dutta, D. K.; Boruah, R. C.; Sandhu, J. S. Indian J. Chem., Sect. B 1986, 25, 350.
35. (i) Okuro, K.; Enna, M.; Miura, M.; Nomura, M. J. Chem. Soc., Chem. Commun. 1993, 1107.
36. (j) Basak, A.; Mahato, T.; Bhattacharya, G.; Mukherjee, B. Tetrahedron Lett. 1997, 38, 643.
37. (k) Basak, A.; Bhattacharya, G.; Bdour, H. M. M. Tetrahedron 1998, 54, 6529.
38. (l) Basak, A.; Ghosh, S. C.; Bhowmick, T.; Das, A. K.; Bertolasi, V. Tetrahedron Lett. 2002, 43, 5499.
39. (m) Basak, A.; Ghosh, S. C. Synlett 2004, 1637.
40. For a recent review on trisoxazolines, see: Zhou, J.; Tang, Y. Chem. Soc. Rev. 2005, 34, 664.
41. (a) Zhou, J.; Tang, Y. J. Am. Chem. Soc. 2002, 124, 9030
42. (b) Zhou, J.; Ye, M.-C.; Huang, Z.-Z. Tang, Y. J. Org. Chem. 2004, 69, 1309.
43. (c) Zhou, J.; Ye, M.-C.; Tang, Y. J. Comb. Chem. 2004, 6, 301.
44. (d) Zhou, J.; Tang, Y. Chem. Commn. 2004, 432.
45. (e) Ye, M.-C.; Li, B.; Zhou, J.; Tang, Y. J. Org. Chem. 2005, 70, 6108.
46. (a) Huang, Z.-Z.; Kang, Y.-B.; Zhou, J.; Ye, M.-C.; Tang, Y. Org. Lett. 2004, 6, 1677.
47. (b) Zhou, J.; Tang, Y. Org. Biomol. Chem. 2004, 2, 429.
48. Ye, M.-C.; Zhou, J.; Huang, Z.-Z. Tang, Y. Chem. Commun. 2003, 2554.
49. For some recent examples on "ligand tuning", see: (a) Reeta, M. T. Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier Pergamon: Amsterdam, Boston, 2004; Vol. 9, p 509.
50. (b) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A.; Nomura, N.; Jin, J.; Park, H.; Nandi, M. Curr. Org. Chem. 2003, 7, 301.
51. (c) Dai, L.-X.; Tu, T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 659.
52. Probably phenylethynylcopper polymer formed. See: Okamoto, Y.; Kundu, S. K. J. Phys. Chem. 1973, 22, 2677.
53. (a) Bellemin-Laponnaz, S.; Gade, L. H. Chem. Commun. 2002, 1286.
54. (b) Bellemin-Laponnaz, S.; Gade, L. H. Angew. Chem., Int. Ed. 2002, 41, 3473.
55. (c) Dro, C.; Bellemin-Laponnaz, S.; Welter, R.; Gade, L. H. Angew. Chem., Int. Ed. 2004, 43, 4479.
56. (d) Seitz, M.; Capacchione, C.; Bellemin-Laponnaz, S.; Wadepohl, H.; Ward, B. D.; Gade, L. H. J. Chem. Soc., Dalton Trans. 2006, 193.
57. Please see the Supporting Information.
58. 2 instead of Cu(I) to produce copper acetylide in the presence of sodium ascorbate. See: Knopfel, T. F.; Carreira, E. M. J. Am. Chem. Soc. 2003, 125, 6054.
59. For Glaser coupling, see: (a) Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.
60. (b) Youngblood, W. J.; Gryko, D. T.; Lammi, R. K.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Org. Chem. 2002, 67, 2111.
61. (c) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
62. For Eglinton coupling, see: (d) Eglinton, G.; Galbraith, A. R. Chem. Ind. 1956, 737.
63. (e) Inouchi, K.; Kabashi, S.; Takimiya, K.; Aso, Y.; Otsubo, T. Org. Lett. 2002, 4, 2533.
64. (f) Fabian, K. H. H.; Lindner, H.-J.; Nimmerfroh, N.; Hafner, K. Angew. Chem., Int. Ed. 2001, 40, 3402.
65. 1H NMR sepectroscopic analysis of the corresponding crude products. Also, 15% yield of (E)-N-benzylidenebenzeneamine was isolated in the reaction of 4a and Sa.
66. For similar ketene intermediate, see: Ahn, C.; Kennington, J. W., Jr.; DeSheong, P. J. Org. Chem. 1994, 59, 6282. In addition, Fu also indicated this processes; see ref 5e.
67. Foltz, C; Stecker, B.; Marconi, G.; Bellemin-Laponnaz, S.; Wade-pohl, H.; Gade, L. H. Chem. Commun. 2005, 5115.