One-pot three-component sysnthesis of α-iminonitriles by IBX/TBAB-mediated oxidative strecker reaction

Organic Letters

Volumn 10, Issue 8, 2008, Pages 1509-1512

  Fontaine, Patrice ^a   Chiaroni, Angle ^a   Masson, Géraldine ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 IODYLBENZOIC ACID; 2-IODOXYBENZOIC ACID; IODOBENZOIC ACID DERIVATIVE; NITRILE; QUATERNARY AMMONIUM DERIVATIVE; TETRABUTYLAMMONIUM;

ARTICLE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

CYCLIZATION; IODOBENZOATES; NITRILES; OXIDATION-REDUCTION; QUATERNARY AMMONIUM COMPOUNDS;

EID: 44449146672     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800199b     Document Type: Article

References (72)

1. (a) De Corte, B.; Denis, J. -M.; De Kimpe, N. J. Org. Chem. 1987, 52, 1147.
2. (b) Roychowdhury, A.; Kumar, V. V.; Bhaduri, A. P. Synth. Commun. 2006, 36, 715.
3. For a recent comprehensive review on imino Diels-Alder reaction, see Heintzelman, G. R.; Meigh, I. R.; Mahajan, Y. R.; Weinreb, S. M. Org. React. 2005, 65, 141.
4. Iminonitrile as part of diene: (a) Sisti, N. J.; Motorina, I. A.; Tran Huu Dau, M.-E.; Riche, C.; Fowler, F. W.; Grierson, D. S. J. Org. Chem. 1996, 61, 3715.
5. (b) Sisti, N. J.; Zeller, E.; Grierson, D. S.; Fowler, F. W. J. Org. Chem. 1997, 62, 2093.
6. (c) Motorina, I. A.; Fowler, F. W.; Grierson, D. S. J. Org. Chem. 1997, 62, 2098.
7. (d) Tarver, J. E.; Terranova, K. M.; Joullié, M. Tetrahedron 2004, 60, 10277.
8. Iminonitrile as dienophile: (a) Middleton, W. J.; Krespan, C. G. J.Org. Chem. 1968, 33, 3625.
9. (b) Amos, D. T.; Renslo, A. R.; Danheiser, R. L. J. Am. Chem. Soc. 2003, 125, 4970.
10. (c) Maloney, K. M.; Danheiser, R. L. Org. Lett. 2005, 7, 3115.
11. Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831.
12. Takahashi, K.; Rimura, S.; Ogawa, Y.; Yamada, K.; Iida, H. Synthesis 1978, 892. Takahashi, K.; Rimura, S.; Ogawa, Y.; Yamada, K.; Iida, H.Synthesis 1978, 892.
13. (a) Boyer, J. H.; Dabek, H. J. Chem. Soc. D 1970, 18, 1204.
14. (b) Boyer, J. H.; Kooi, J. J. Am. Chem. Soc. 1976, 98, 1099.
15. (c) De Kimpe, N.; Verhé, R.; De Buyck, L.; Chys, J.; Schamp, N. Synthesis 1978, 895.
16. (d) Ksander, G.; Bold, G.; Lattmann, R.; Lehmann, C; Früh, T.; Xiang, Y.-B.; Inomata, K.; Buser, H.-P.; Schreiber, J.; Zass, E.; Eschenmoser, A. Helv. Chim. Acta 1987, 70, 1115.
17. (e) Drenkard, S.; Ferris, J.; Eschenmoser, A. Helv. Chim. Acta 1990, 73, 1373.
18. Smith, J. G.; Irwin, D. C. Synthesis 1978, 894.
19. (a) Ducta, D. K.; Prajapati, D.; Sandhu, J. S.; Baruah, J. N. Synth. Commun. 1985, 15, 335.
20. (b) Konwar, D.; Goswami, B. N.; Borthakur, N. J. Chem. Res. Synop. 1999, 242.
21. Pochat, F. Tetrahedron Lett. 1981, 22, 955.
22. (a) Saegusa, T.; Taka-Ishi, N.; Ito, Y. J. Org. Chem. 1969, 34, 4040.
23. (b) Pellissier, H.; Gil, G. Tetrahedron Lett. 1989, 30, 171.
24. (c) Tobisu, M.; Kitajima, A.; Yoshioka, S.; Hyodo, I.; Ospita, M.; Chatani, N. J. Am. Chem. Soc. 2007, 129, 11431.
25. Sandhu, J. S.; Mohan, S.; Kapoor, A. L. Chem. Ind. (London) 1971,5, 152.
26. (13)Jursic, B. S.; Douelle, F.; Bowdy, K.; Stevens, E. D. Tetrahedron Lett. 2002, 43, 5361.
27. (a) Ngouansavanh, T.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46,5775.
28. (b) Ngouansavanh, T.; Zhu, J. Angew. Chem., Int. Ed. 2006, 45, 3495.
29. For a recent overview, see: Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Acc. Chem. Res. 2005, 38, 851.
30. (a) Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272.
31. (b) Richardson, R. D.; Zayed, J. M.; Altermann, S.; Smith, D.; Wirth, T. Angew. Chem., Int. Ed. 2007, 46, 6529 and references therein.
32. (c) Moorthy, J. N.; Singhal, N.; Senapati, K. Org. Biomol. Chem. 2007, 5, 767.
33. (d) Moorthy, J. N.; Singhal, N.; Senapati, K. Tetrahedron Lett. 2008, 49, 80.
34. (17)Gallen, J.; Goumont, R.; Clark, T.; Terrier, F.; Williams, C. M. Angew. Chem., Int. Ed. 2006, 45, 2929.
35. (a) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602.
36. (b) Groger, H. Chem. Rev. 2003, 103, 2795.
37. (c) Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359.
38. (d) Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
39. (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem., Int. Ed. 2003, 42, 4077.
40. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192.
41. For highlights, see: (a) Wirth, T. Angew. Chem., Int. Ed. 2001, 40, 2812.
42. (b) Wirth, T.; Angew. Chem., Int. Ed. 2006, 45, 4402.
43. (a) Martinez, R.; Ramón, D. J.; Yus, M. Tetrahedron Lett. 2005, 46, 8472.
44. (b) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081.
45. (c) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389.
46. Quaternary ammonium salt were known to be beneficial in some IBX-mediated transformations, see: (a) Tohma, H.; Takizawa, S.; Watanabe, H.; Fukuoka, Y.; Maegawa, T.; Kita, Y. J. Org. Chem. 1999, 64, 3519.
47. (b) Tohma, H.; Takizawa, S.; Mori oka, H.; Maegawa, T.; Kita, Y. Chem. Pharm. Bull. 2000, 48, 445.
48. (c) Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. J. Org. Chem. 2003, 68, 5422.
49. (d) Zhu, J.; Germani, A. G.; Porco, Jr. J. A. Angew. Chem., Int. Ed. 2004, 43, 1239.
50. (e) Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. Synlett 2005, 1483.
51. (f) Kuhakarn, C; Kittigowittana, K.; Pohmakotr, M.; Reutrakul, V. Tetrahedron 2005, 61, 8995.
52. (g) Kuhakarn, C.; Kittigowittana, K.; Ghabkham, P.; Pohmakotr, M.; Reutrakul, V. Tetrahedron 2005, 61, 8995.
53. (h) Ozanne-Beaudenon, A.; Quideau, S. Tetrahedron Lett. 2006, 47, 5869.
54. (i) Bhalerao, D. S.; Mahajan, U. S.; Chaudhari, K. H.; Akamanchi, K. G. J. Org. Chem. 2007, 72, 662.
55. (j) Potassium iodide as additive: Pan, Z.-L.; Liu, X.-Y.; Liang, Y.-M. Tetrahedron Lett. 2004, 45, 4101.
56. (a) Royer, L.; De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2005, 46, 4595.
57. (b) Masdeu, C; Gómez, E.; Williams, N. A. O.; Lavilla, R. Angew. Chem., Int. Ed. 2007, 46, 3043.
58. (a) Andrés, J. M.; Barrio, R;, Martinez, M. A.; Pedrosa, R.; Pérez-Encabo, A. J. Org. Chem. 1996, 1, 4210.
59. (b) Laïb, T.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1997, 38, 1771.
60. (c) Andres, J. M.; Pedrosa, R. Tetrahedron 1998, 54, 5607.
61. (d) Laïb, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709.
62. The formation of the minor product results from partial epimerization of N,N-dibenzyl serinal. The chiral amine is configurationally stable as shown in the formation of 1f.
63. De Kimpe, N.; Verhé, R.; de Buyck, L.; Hasma, H.; Schamp, N. Tetrahedron 1976, 32, 3063.
64. CDC-668053 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc-can.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Center, 12 Union Road, CambridgeCB21EZ, UK; Fax: (+44)1223-336033; or deposit@ccdc.cam.ac.uk.
65. For leading references on the biological activity of indolizidine alkaloids, see: (a) Michael, J. P. Nat. Prod. Rep. 2007, 24, 3001.
66. (b) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press, Inc.: San Diego, 1993; Vol. 44, Chapter 3.
67. (a) Nicolaou, K. C.; Zhong, Y-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 625.
68. (b) Nicolaou, K. C; Baran, P. S.; Kranich, R.; Zhong, Y-L.; Sugita, K.; Zou, N. Angew. Chem., Int. Ed. 2001, 40, 202.
69. (a) Lee, J.; U, J. S.; Blackstock, S. C.; Cha, J. K. J. Am. Chem. Soc. 1997, 119, 10241.
70. (b) Itoh, T.; Kaneda, K.; Teranishi, S. Tetrahedron Lett. 1975, 2801.
71. 5-Exo-cyclization of δ,ω-unsaturated aminium cation radical, see: Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc. 1987, 109, 3163.
72. Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Bolz, J. T.; Mismash, B.; Woodward, J. K.; Simonsen, A. J. Tetrahedron Lett. 1995, 36, 7975.