Chiral salen - Aluminum complex as a catalyst for enantioselective α-addition of isocyanides to aldehydes: Asymmetric synthesis of 2-(1-hydroxyalkyl)-5-aminooxazoles

Organic Letters

Volumn 9, Issue 18, 2007, Pages 3615-3618

  Wang, Shi Xin ^a   Wang, Mei Xiang ^a   Wang, De Xian ^a   Zhu, Jieping ^b  

^a INSTITUTE OF CHEMISTRY   (China)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2-CYANOACETAMIDE; ALDEHYDE; ALKANE; CYANIDE; CYANOACETAMIDE; ETHYLENEDIAMINE DERIVATIVE; NITRILE; ORGANOMETALLIC COMPOUND; OXAZOLE DERIVATIVE; SALEN ALUMINUM COMPLEX; SALEN-ALUMINUM COMPLEX; UNCLASSIFIED DRUG;

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

ALDEHYDES; ALKANES; CATALYSIS; CYANIDES; ETHYLENEDIAMINES; MOLECULAR STRUCTURE; NITRILES; ORGANOMETALLIC COMPOUNDS; OXAZOLES; STEREOISOMERISM;

EID: 34548534037     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7014658     Document Type: Article

References (67)

1. Banfi, L.; Riva, R. Organic Reactions; Charette, A. B., Ed.; John Wiley & Sons, Inc.: New York, 2005; Vol. 65, pp 1-140.
2. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
3. (a) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80.
4. (b) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471-1499.
5. (c) Tempest, P. Curr. Opin. Drug Discovery Dev. 2005, 8, 776-788.
6. (d) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144.
7. (e) Dömling, A. Chem. Rev. 2006, 106, 17-89.
8. (a) Marcaccini, S.; Miguel, D.; Torroba, T.; Garcia-Valverde, M. J. Org. Chem. 2003, 68, 3315-18.
9. (b) Frey, R.; Galbraith, S. G.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536-1538.
10. (c) Cuny, G.; Gamez-Montano, R.; Zhu, J. Tetrahedron 2004, 60, 4879-4885.
11. (d) Krishna, P. R.; Dayaker, G.; Reddy, P. V. N. Tetrahedron Lett. 2006,47, 5977-5980.
12. (a) Kunz, H.; Pfrengle, W. J. Am. Chem. Soc. 1988, 110, 651-652.
13. (b) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337.
14. (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133.
15. (d) Basso, A.; Banfi, L.; Riva, R.; Guanti, G. J. Org. Chem. 2005, 70, 576-580.
16. Banfi, L.; Basso, A.; Guanti, G.; Banfi, L. Asymmetric Isocyanide-based MCRs. In Multicomponent reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005; pp 1-32.
17. Reviews: (a) Seayad, J.; List, B. Catalytic Asymmetric Multicomponent Reactions. In Multicomponent reaction; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005; pp 277-299.
18. (b) Ramón, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602-1634.
19. (c) D. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581.
20. (a) Denmark, S.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825-7827.
21. (b) Denmark, S.; Fan, Y. J. Org. Chem. 2005, 70, 9667-9676.
22. Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 4021-4024.
23. Andreana, P. R.; Liu, C. C.; Schreiber, S. L. Org. Lett. 2004, 6, 4231-4233.
24. Wang, S.-X.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Eur. J Org. Chem. 2007, 4076-4080.
25. The α-isocyanoacetamides are easily available; see: (a) Fayol, A.; Housseman, C.; Sun, X.; Janvier, P.; Bienaymé, H.; Zhu, J. Synthesis 2005, 161-165.
26. (b) Housseman, C.; Zhu, J. Synlett 2006, 1777-1779.
27. (c) Dömling, A.; Beck, B.; Fuchs, T.; Yazbak, A. J. Comb. Chem. 2006, 8, 872-880.
28. (a) Sun, X.; Janvier, J.; Bienaymé, H.; Zhu, J. Org. Lett. 2001, 3, 877-880.
29. (b) Janvier, P.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 2560-2567.
30. (c) Janvier, P.; Bois-Choussy, M.; Bienaymé, H.; Zhu, J. Angew. Chem., Int. Ed. 2003, 42, 811-814.
31. (d) Pirali, T.; Tron, G. C.; Zhu, J. Org. Lett. 2006, 8, 4145-4148.
32. Selected X-ray structures, see: (a) Brackemeyer, T.; Erker, G.; Fröhlich, R. Organometallics 1997, 76, 531-536.
33. (b) Jacobsen, H.; Berke, H.; Döring, S.; Kehr, G.; Erker, G.; Fröhlich, R.; Meyer, O. Organometallics 1999, 18, 1724-1735.
34. Selected examples: (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406.
35. (b) Tongi, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649-1664.
36. (c) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett. 1996, 37, 4969-4972.
37. (d) Lin, Y.-R.; Zhou, X.-T.; Dai, L.-X.; Sun, J. J. Org. Chem. 1997, 62, 1799-1803.
38. (e) Grigg, R.; Lansdell, M. I.; Thornton-Pett, M. Tetrahedron 1999, 55, 2025-2044.
39. (f) Takaya, H.; Kojima, S.; Murahashi, S. Org. Lett. 2001, 3, 421-424.
40. (g) Bon, R. S.; Van Vliet, B.; Sprenkels, N. E.; Schmitz, R. F.; De Kanter, F. J. J.; Stevens, C. V.; Swart, M.; Bickelhaupt, F. M.; Groen, M. B.; Orru, R. V. A. J. Org. Chem. 2005, 70, 3542-3553.
41. (h) Kanazawa, C.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2006, 128, 10662-10663 and references cited therein.
42. Morrison, D. J.; Piers, W. E. Org. Lett. 2003, 5, 2857-2860.
43. (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315-5316.
44. (b) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960.
45. (c) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443. Reviews:
46. (d) Larrow, J. F.; Jacobsen, E. N. Top. Organomet Chem. 2004, 6, 123-152.
47. (e) Structure of group 13 compounds incorporating salen ligands: Atwood, D. A.; Harvey, M. J. Chem. Rev. 2001, 101, 37-52.
48. The competing coordination of Lewis basic solvents to metal center might account for the reduced enantioselectivity.
49. Wang, Q.; Ganem, B. Tetrahedron Lett. 2003, 44, 6829-6832.
50. Lewis acid catalyzed reaction of 5-alkoxyoxazole with aldehyde to afford the oxazoline was known, for enantioselective version, see the following. BIINAP-Al complex-catalyzed: Suga, H.; Ikai, K.; Ibata, T. J. Org. Chem. 1999, 64, 7040-7047. Salen-Al complex-catalyzed:
51. (b) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888.
52. Direct aldol reaction of α-isocyanoacetamide with aldehyde in the presence of chiral gold catalyst to afford chiral oxazoline was known; see: (a) Ito, Y.; Sawamura, M.; Kobayashi, M.; Hayashi, T. Tetrahedron Lett. 1988, 29, 6321-6324.
53. (b) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684.
54. For a recent comprehensive review on the chiral titanium complex, see: Ramón, D. J.; Yus, M. Chem. Rev. 2006, 106, 2126-2208.
55. To heterocycles: (a) Gámez-Montaño, R.; Zhu, J. J. Chem. Soc., Chem. Commun. 2002, 2448-2449.
56. (b) Fayol, A.; Zhu, J. Angew. Chem., Int. Ed. 2002, 47, 3633-3635.
57. (c) Janvier, P.; Bienaymé, H.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 4291-4294.
58. (d) Gámez-Montaño, R.; González-Zamora, E.; Potier, P.; Zhu, J. Tetrahedron 2002, 58, 6351-6358.
59. (e) Fayol, A.; Zhu, J. Org. Lett. 2005, 7, 239-242.
60. (f) Tron, G. S.; Zhu, J. Synlett 2005, 532-534.
61. (g) Bonne, D.; Dekhane, M.; Zhu, J. Org. Lett. 2005, 7, 5285-5288.
62. (h) Zhao, G.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2001, 123, 6700-6701.
63. (i) Bughin, C.; Zhao, G.; Bienaymé, H.; Zhu, J. Chem-Eur. J. 2006, 12, 1174-1184.
64. (j) Bughin, C.; Masson, G.; Zhu, J. J. Org. Chem. 2007, 72, 1826-1829.
65. Reviews on the chemistry of oxazole, see: (a) Karpeiskii, M. Y.; Florent'ev, V. L. Russ. Chem. Rev. 1969, 38, 540-546.
66. (b) Jacobi, P. A. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: London, 1992; Vol 2, pp 251-298.
67. (c) V Yeh, V. S. C. Tetrahedron 2004, 60, 11995-12042.