Convenient transformation of optically active nitroalkanes into chiral aldoximes and nitriles

Angewandte Chemie - International Edition

Volumn 44, Issue 4, 2005, Pages 612-615

  Czekelius, Constantin ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Chirality; Nitro compounds; Oximes; Reduction; Synthetic methods

Indexed keywords

ENVIRONMENTAL IMPACT; METALS; PARAFFINS; REACTION KINETICS;

METAL IMPURITIES; NITRILES; NITROALKANES;

AROMATIC HYDROCARBONS;

ALDOXIME; NITRILE; NITROALKANE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; OPTICAL ROTATION; POLARIMETRY; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 13244258496     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461879     Document Type: Article

References (63)

1. a) N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001;
2. b) V. V. Perekalin, E. S. Lipina, V. M. Berestovitskaya, D. A. Efremov, Nitroalkenes, Wiley, Chichester, 1994;
3. c) Nitro Compounds-Recent Advances in Synthesis and Chemistry: Organic Nitro Chemistry Series (Eds.: H. Feuer, A. T. Nielsen), VCH, Weinheim, 1990;
4. d) D. Seebach, E. W. Colvin, F. Lehr, T. Weller, Chimia 1979, 33, 1.
5. a) For an excellent review, see: O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877;
6. b) H. Schäfer, D. Seebach, Tetrahedron 1995, 51, 2305;
7. c) N. Sewald, V. Wendisch, Tetrahedron: Asymmetry 1998, 9, 1341;
8. d) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192;
9. e) D. M. Mampreian, A. H. Hoveyda, Org. Lett. 2004, 6, 2829;
10. f) A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262;
11. g) A. Duursma, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2003, 125, 3700;
12. h) H. Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906;
13. i) H. Choi, Z. Hua, I. Ojima, Org. Lett. 2004, 6, 2689;
14. j) T. Ishii, S. Fujioka, Y. Sekiguchi, H. Kotsuki, J. Am. Chem. Soc. 2004, 126, 9558;
15. k) J. M. Betancourt, C. F. Barbas III, Org. Lett. 2001, 3, 3737;
16. l) C. Czekelius, E. M. Carreira, Angew. Chem. Int. Ed. 2003, 42, 4793; Angew. Chem. 2003, 115, 4941.
17. l) C. Czekelius, E. M. Carreira, Angew. Chem. Int. Ed. 2003, 42, 4793; Angew. Chem. 2003, 115, 4941.
18. a) H. Sasai, T. Suzuki, S. Arai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1992, 114, 4418;
19. b) H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 60, 7388;
20. c) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1236;
21. c) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1236;
22. d) T. Arai, Y. M. A. Yamada, N. Yamamoto, H. Sasai, M. Shibasaki, Chem. Eur. J. 1996, 2, 1368;
23. e) H. Sasai, N. Itoh, T. Suzuki, M. Shibasaki, Tetrahedron Lett. 1993, 34, 855;
24. f) H. Sasai, Y. M. Yamada, T. Suzuki, M. Shibasaki, Tetrahedron 1994, 50, 12313;
25. g) H. Sasai, T. Suzuki, N. Itoh, S. Arai, M. Shibasaki, Tetrahedron Lett. 1993, 34, 2657;
26. h) B. M. Trost, V. S. C. Yeh, Angew. Chem. 2002, 114, 889; Angew. Chem. Int. Ed. 2002, 41, 861;
27. h) B. M. Trost, V. S. C. Yeh, Angew. Chem. 2002, 114, 889; Angew. Chem. Int. Ed. 2002, 41, 861;
28. i) B. M. Trost, V. S. C. Yeh, H. Ito, N. Bremeyer, Org. Lett. 2002, 4, 2621;
29. j) D. A. Evans, D. Seidel, M. Rueping, H. W. Lam, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2003, 125, 12962.
30. a) J. von Braun, W. Sobecki, Ber. Dtsch. Chem. Ges. 1911, 44, 2526;
31. b) J. von Braun, E. Danziger, Ber. Dtsch. Chem. Ges. 1913, 46, 103;
32. c) M. Bartra, P. Romea, F. Urpí, J. Vilarasa, Tetrahedron 1990, 46, 587;
33. d) D. Edmont, D. M. Williams, Tetrahedron Lett. 2000, 41, 8581;
34. e) C. C. Hughes, D. Trauner, Angew. Chem. 2002, 114, 4738; Angew. Chem. Int. Ed. 2002, 41, 4556;
35. e) C. C. Hughes, D. Trauner, Angew. Chem. 2002, 114, 4738; Angew. Chem. Int. Ed. 2002, 41, 4556;
36. f) D. H. R. Barton, I. Fernandez, C. S. Richard, S. Z. Zard, Tetrahedron 1987, 43, 551;
37. g) D. Albanese, D. Landini, M. Peno, G. Pozzi, Synth. Commun. 1990, 20, 965;
38. h) D. Albanese, D. Landini, M. Penseo, Synthesis 1990, 333.
39. For other metal-mediated reductions of nitroalkanes to oximes, see: a) M. Hudlický, Reductions in Organic Chemistry, Ellis Horwood, Chichester, 1984;
40. b) K. Johnson, E. F. Degering, J. Am. Chem. Soc. 1939, 61, 3194;
41. c) J. E. McMurry, J. Melton, J. Org. Chem. 1973, 38, 4367;
42. d) Y. Akita, M. Inaba, H. Uchida, A. Ohta, Synthesis 1977, 792.
43. a) H. B. Hass, M. L. Bender, J. Am. Chem. Soc. 1949, 71, 1767;
44. b) H. B. Hass, M. L. Bender, J. Am. Chem. Soc. 1949, 71, 3482;
45. c) C. D. Nenitzescu, D. A. Isacescu, Ber. Dtsch. Chem. Ges. B. 1930, 63, 2484;
46. d) R. Filler, H. Novar, J. Org. Chem. 1960, 25, 733;
47. e) C. F. Bigge, J. T. Drummond, G. Johnson, T. Malone, A. W. Probert, Jr., F. W. Marcoux, L. L. Coughenour, L. J. Brahce, J. Mol. Chem. 1989, 32, 1580;
48. f) T. C. Bedard, J. Y. Corey, L. D. Lange, N. P. Rath, J. Organomet. Chem. 1991, 401, 261;
49. g) W. Kirmse, W. Konrad, D. Schnitzler, J. Org. Chem. 1994, 59, 3821.
50. For the transformation of phenylnitromethane into benzaldehyde oxime, see: L. Weisler, R. W. Helmkamp, J. Am. Chem. Soc. 1945, 67, 1167.
51. 4NI (5 mol%) in THF at room temperature for 6 h.
52. a) C. Schöpf, G. Lehmann, Justus Liebigs Ann. Chem. 1935, 518, 1;
53. b) J. Tadanier, C.-M. Lee, D. Whittern, N. Wideburg, Carbohydr. Res. 1990, 201, 185.
54. a) J. W. Bode, N. Fraefel, D. Muri, E. M. Carreira, Angew. Chem. 2001, 113, 2128; Angew. Chem. Int. Ed. 2001, 40, 2082;
55. a) J. W. Bode, N. Fraefel, D. Muri, E. M. Carreira, Angew. Chem. 2001, 113, 2128; Angew. Chem. Int. Ed. 2001, 40, 2082;
56. b) L. D. Fader, E. M. Carreira, Org. Lett. 2004, 6, 2485;
57. c) For a review of asymmetric 1,3-dipolar cycloaddition reactions, see: K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863.
58. a) W. Steinkopf, L. Bohrmann, Ber. Dtsch. Chem. Ges. 1908, 41, 1044;
59. b) L. Hellerman, R. L. Garner, J. Am. Chem. Soc. 1946, 68, 819;
60. c) A. B. Charette, A. Gagnon, M. Janes, C. Mellon, Tetrahedron Lett. 1998, 39, 5147;
61. d) R. Tsang, B. Fraser-Reid, J. Am. Chem. Soc. 1986, 108, 2116;
62. e) J. Marco-Contelles, P. Gallego, M. Rodríguez-Fernández, N. Khiar, C. Destabel, M. Bernabé, A. Martínez-Grau, J. L. Chiara, J. Org. Chem. 1997, 62, 7397.
63. For the hydrocyanation of monosubstituted vinylarenes, see: T. V. Rajanbabu, A. L. Casalnuovo, J. Am. Chem. Soc. 1996, 118, 6325.