Reaction control in the organocatalytic asymmetric one-pot, three-component reaction of aldehydes, diethyl α-aminomalonate and nitroalkenes: Toward diversity-oriented synthesis

Chemistry - A European Journal

Volumn 14, Issue 32, 2008, Pages 9873-9877

  Liu, Yan Kai ^a   Liu, Hao ^a   Du, Wei ^a   Yue, Lei ^a   Chen, Ying Chun ^a,b  

^a SICHUAN UNIVERSITY   (China)

^b SICHUAN UNIVERSITY   (China)

Author keywords

Azomethine ylides; Cycloaddition; Michael addition; Nitroalkenes; Organocatalysis

Indexed keywords

ALDEHYDE; ALKENE; DIETHYL AMINOMALONATE; MALONIC ACID DERIVATIVE; NITRO DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION;

ALDEHYDES; ALKENES; CATALYSIS; CYCLIZATION; MALONATES; MOLECULAR STRUCTURE; NITRO COMPOUNDS;

EID: 55449131123     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801410     Document Type: Article

References (68)

1. For reviews, see: a) M. J. O'Donnell, Acc. Chem. Res. 2004, 37, 506-517;
2. b) K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013-3028;
3. c) T. Ooi, K.. Maruoka, Aldrichimica Acta 2007, 40, 77-86: for selected examples, see:
4. d) E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347-5350:
5. e) F.-Y. Zhang, E. J. Corey, Org. Lett. 2000, 2, 1097-1100;
6. f) S. Arai, R. Tsuji, A. Nishida, Tetrahedron Lett. 2002, 43, 9535-9537;
7. g) T. Shibuguchi, Y. Fukuta, Y. Akachi, A. Sekine, T. Ohshima, M. Shihasaki, Tetrahedron Lett. 2002, 43, 9539-9543;
8. h) B. Lygo, B. Allbutt, E. H. M. Kirton, Tetrahedron Lett. 2005, 46, 4461-4464;
9. i) T. Ishikawa, Y. Araki, T. Kumamoto, T. Isobe, H. Seki, K. Fukuda, Chem. Commun. 2001, 245-246;
10. j) T. Akiyama, M. Hara, K. Fuchibe, S. Sakamoto, K. Yamaguchi, Chem. Commun. 2003, 1734-1735;
11. k) S. Kobayashi, T. Tsubogo, S. Saito, Y. Yamashita, Org. Lett. 2008, 10, 807-809.
12. For reviews, see: a) K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-910;
13. b) I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765-2810;
14. c) C. Nájera, J. M. Sansano, Angew. Chem. 2005, 117, 6428-6432;
15. Angew. Chem. Int. Ed. 2005, 44, 6272-6276;
16. d) O. Pandey, P. Banerjee, S. R. Cadre. Chem. Rev. 2006, 106. 4484-4517;
17. e) L. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887-2902; for selected examples, see:
18. f) A. S. Gothelf. K. V. Gothelf, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2002, 114, 4410-4412;
19. Angew. Chem. Int. Ed. 2002, 41, 4236-4238;
20. g) J. M. Longmire, B. Wang, X. Zhang. J. Am. Chem. Soc. 2002, 124, 13400-13401;
21. h) Y. Oderaotoshi, W. Cheng, S. Fujitomi, Y. Kasano, S. Minakata, M. Komatsu, Org. Lett. 2003, 5, 5043-5046;
22. i) S. Cabrera, R. G. Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2005, 127, 16394-16395;
23. j) T. Llamas, R. G. Arrayás, J. C. Carretero. Org. Lett. 2006, 8, 1795-1798;
24. k) O. Dogan, H. Koyuncu, P. Garner, A. Bulut, W. J. Youngs, M. Panzner, Org. Lett. 2006, 8, 4687-4690;
25. l) W. Zeng, G.-Y. Chen, Y.-O. Zhou, Y.-X. Li, J. Am. Chem. Soc. 2007, 129, 750-751;
26. m) J.L. Vicario, S. Reboredo, D. Badía, L. Carrillo, Angew. Chem. 2007, 119, 5260-5262;
27. Angew. Chem. Int. Ed. 2007, 46, 5168-5170.
28. For examples of [3+2] cycloaddition with in situ formed α-imino esters, see: a) X.-H. Chen. W.-Q. Zhang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 5652-5653;
29. b) I. Ibrahem, R. Rios, J. Vesely, A. Córdova, Tetrahedron Lett. 2007, 48. 6252-6257;
30. c) C. Chen, X. Li, S. L. Schreiber, J. Am. Chem. Soc. 2003, 125, 10174-10175; for related cycloaddition of in situ formed nitrones, see:
31. d) R. Rios. I. Ibrahem, J. Vesely, G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2007, 48, 5701-5705;
32. e) I. S. Young, M. A. Kerr, Org. Lett. 2004, 6, 139-141.
33. Either the Michael adducts or the [3+2] cycloaddition products from α-imino esters could be produced catalyzed by chiral calcium complexes, but not with the same substrates, see: S. Saito, T. Tsubogo. S. Kobayashi, J. Am. Chem. Soc: 2007, 129, 5364-5365.
34. For a review on diversity-oriented synthesis (DOS), see: M. D. Burke, S. L. Schreiber. Angew. Chem. 2004, 116, 48-60;
35. Angew. Chem. Int. Ed. 2004, 43, 46-58.
36. For a recent review on organocatalytic enantioselective multicomponent reactions, see: a) G. Guillena, D. J. Ramón, M. Yus. Tetrahedron: Asymmetry 2007, 18, 693-700; for selected examples, see:
37. b) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337;
38. c) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833;
39. d) D. B. Ramachary, C. F. Barbas, III. Chem. Eur. J. 2004, 10, 5323-5331;
40. e) R. I. Stoter, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86;
41. f) X.-H. Chen, X.-Y. Xu, H. Liu, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 2006, 128, 14802-14803;
42. g) D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861-863.
43. For selected examples, see: a) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673;
44. b) B.-J. Li, L. Jiang, M. Liu, Y.-C. Chen, L.-S. Ding, Y. Wu, Synlett 2005, 603-606;
45. c) A. Berkessel, F. Cleemann, S. Mukherjee, T. N. Müller, J. Lex, Angew. Chem. 2005, 117, 817-821;
46. Angew. Chem. Int. Ed. 2005, 44, 807-811;
47. d) A. Berkessel, F. Cleemann, S. Mukherjee, Angew. Chem. 2005, 117, 7632-7635;
48. Angew. Chem. Int. Ed. 2005, 44, 7466-7469;
49. e) Y. Hoashi, T. Okino, Y. Takemoto, Angew. Chem. 2005, 117, 4100-4103;
50. Angew. Chem. Int. Ed. 2005, 44, 4032-4035;
51. f) T. Inokuma, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2006, 128, 9413-9419;
52. g) J. Wang, H. Li, L. Zu, W. Jiang, H. Xie, W. Duan, W. Wang, J. Am. Chem. Soc. 2006, 128, 12652-12653;
53. h) T.-Y. Liu, H.-L. Cui, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, J. Am. Chem. Soc. 2007, 129, 1878-1879;
54. i) S. J. Zuend, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 15872-15883; for a recent review on thiourea and urea catalysis, see:
55. j) A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743.
56. A thiourea-catalyzed three-component asymmetric acyl-Strecker reaction has been recently reported, see: S. C. Pan, B. List, Org. Lett. 2007, 9, 1149-1151.
57. For studies on [3+2] cycloadditions of azomethine ylides and nitroalkenes, see: a) S. Vivanco, B. Lecea, A. Arrieta, P. Prieto, I. Morao, A. Linden, F. P. Cossío, J. Am. Chem. Soc. 2000, 122, 6078-6092;
58. b) X.-X. Yan, Q. Peng, Y. Zhang, K. Zhang, W. Hong, X.-L. Hou, Y.-D. Wu, Angew. Chem. 2006, 118, 2013-2017;
59. Angew. Chem. Int. Ed. 2006, 45, 1979-1983.
60. One-pot, three-component cycloaddition of aldehydes, diethyl α-aminomalonates and nitroalkenes has been very recently reported with exo-selectivity in racemic form without catalysts. Thiourea catalysts reduce the diastereolselectivity significantly. See: L. Crovetto, R. Rios, Synlett 2008, 1840-1844.
61. a) O. Tsuge, S. Kanemasa, M. Yoshioka, J. Org. Chem. 1988, 53, 1384-1391;
62. b) C. Alemparte, G. Blay, K. A. Jørgensen, Org. Lett. 2005, 7, 4569-4572;
63. c) The combination of thiourea-tertiary amine 1a and AgF could not catalyze the dipolar cycloaddition because of the preferable formation of the thiourea-Ag complex. However, urea-tertiary amine 1b-AgF promoted the cycloaddition (Table 1, entry 3).
64. X. Xu, T. Yabuta, P. Yuan, Y. Takemoto, Synlett 2006, 137-140.
65. The absolute configuration of 4 has not yet been determined. It was assigned based on the concerted catalytic mode by Takemoto et al.: T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J, Am. Chem. Soc. 2005, 127, 119-125. Please see Supporting Information.
66. The direct Michael addition of diethyl α-aminomalonate to nitroalkenes, catalyzed by lb, could not proceed in the absence of aldehydes.
67. The Michael adducts have been proposed as intermediates in the [3+2] cycloaddition of azomethine ylides. See ref. 4 and ref. 9.
68. Thiourea-pyrrole catalysts 1h-m were prepared in a similar procedure to 1g, reported by Taylor and Jacobsen. See: M.S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 10558-10559.