A three-component reaction based on a remote-group-directed dynamic kinetic aza-Michael addition: Stereoselective synthesis of imidazolidin-4-ones

Chemistry - A European Journal

Volumn 16, Issue 10, 2010, Pages 2972-2976

  Xu, Zhenghu ^a   Buechler, Tyler ^a   Wheeler, Kraig ^b   Wang, Hong ^a  

^a MIAMI UNIVERSITY   (United States)

^b EASTERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Br nsted acid catalysis; Diastereoselectivity; Dynamic kinetic alkylation; Michael addition; Multicomponent reactions

Indexed keywords

ACID CATALYSIS; DIASTEREO-SELECTIVITY; MICHAEL ADDITION; MICHAEL ADDITIONS; MULTI-COMPONENT REACTIONS;

ACIDS; ALDEHYDES; ALKYLATION; AMIDES; CATALYSIS; HYDROCARBONS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ADDITION REACTIONS;

HETEROCYCLIC COMPOUND; HYDANTOIN DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYLATION; AZA COMPOUNDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HYDANTOINS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77649218587     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903508     Document Type: Article

References (70)

1. a) G. Schneider, U. Fechner, Nat. Rev. Drug Discovery 2005, 4, 649-663;
2. b) S. B. Mhaske, N. P. Argade, Tetrahedron 2006, 62, 9787-9826.
3. N. Vale. M. S. Collins, J. Gut. R. Ferraz, P. J. Rosenthal, M. T. Cushion, R. Moreira. P. Gomes. Bioorg. Med. Chem. Lett. 2008, 18, 485-488.
4. a) N. Vale. J. Matos. J. Gut, F. Nogueira. V. do Rosario, P.J. Rosenthal, R. Moreira. P. Gomes, Bioorg. Med. Chem. Lett. 2008, 18, 4150-4153;
5. b) P. Gomes, M. J. Araujo, M. Rodrigues, N. Vale, Z. Azevedo, J. Iley. P. Chambel. J. Morais, R. Moreira. Tetrahedron 2004, 60, 5551-5562;
6. c) M. J. Araújo. J. Bom. R. Capela, C. Casimiro, P. Chambel. P. Gomes, J. Iley. F. Lopes. J. Morais. R. Moreira. E. de Oliveira. V. do Rosario, N. Vale, J. Med. Chem. 2005, 48, 888-892.
7. J. Chen. Z. Wang, Y. Lu, J. T. Dalton, D. D. Miller, W. Li. Bioorg. Med. Chem. Lett. 2008, 18, 3183-3187.
8. M. Rinnova. A. Nefzi, R. A. Houghten, Tetrahedron Lett. 2002, 43, 2343-2346.
9. a) S. W. Baldwin, A. Long, Org. Lett. 2004, 6, 1653-1656;
10. b) R. Polt. D. Seebach, J. Am. Chem. Soc. 1989, 111, 2622-2632;
11. c) D. Seebach, E. Dziadulewicz, L. Behrendt, S. Cantoreggi, R. Fitzi, Liebigs Ann. Chem. 1989, 1215-1232;
12. d) J. P. Bégué. D. Bonnet-Delpon. A. Chennoufi, M. Ourevitch, K. S. Ravikumar. M. H. Rock. J. Fluorine Chem. 2001, 107, 275-279:
13. e) R. Fitzi. D. Seebach, Angew. Chem. 1986, 98, 363-364;
14. Angew. Chem. Int. Ed. Engl. 1986, 25, 345-346;
15. f) D. Seebach, E. Juaristi, D. D. Miller, C. Schickli. T. Weber. Helv. Chim. Acta 1987, 70, 237-261;
16. g) E. Juaristi, O. Garcia-Barradas, Enantioselective Synthesis of beta-Amino Acids (Ed.: E. Juaristi), Wiley-VCH, Weinheim, 1997, pp. 139-149.
17. C.C. Hughes, D. Trauner, Angew. Chem. 2002, 114, 4738-4741;
18. Angew. Chem. Int. Ed. 2002, 41, 4556-4559.
19. a) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875;
20. b) K. A. Ahrendt. C. J. Borths, D. W. C. MacMillan. J. Am. Chem. Soc. 2000, 122, 4243-4244.
21. X. M. Chen. H. Wei, Y. Y. Chen, X. S. Li. Helv. Chim. Acta 2009, 92, 1550-1557.
22. a) C. A. Panetta. M. Peshimam, J. Org. Chem. 1972, 37, 302;
23. b) P. Chambel, R. Capela, F. Lopes, J. Iley. J. Morais, L. Gouveia, J. R. B. Gomes, P. Gomes, R. Moreira, Tetrahedron 2006, 62, 9883-9891.
24. D. B.-I. Uri Zehavi, J. Org. Chem. 1961, 26, 1097-1101.
25. R. Ferraz. J. R. B. Gomes, E. de Oliveira, R. Moreira, P. Gomes. J. Org. Chem. 2007, 72, 4189-4197.
26. a) M. Rueping. C. Azap, Angew. Chem. 2006, 118, 7996-7999:
27. Angew. Chem. Int. Ed. 2006, 45, 7832-7835;
28. for reviews, see: b) P. R. Krishna. A. Sreeshailam, R. Srinivas, Tetrahedron 2009, 65, 9657-9672;
29. c) D. Enders, C. Wang, J. X. Liebich, Chem. Eur. J. 2009, 15, 11058-11076;
30. d) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035.
31. a) C. Enkisch, C. Schneider, Eur. J. Org. Chem. 2009, 5549-5564;
32. b) P. G. Lima, L. C. Sequeira, P. R. R. Costa, Tetrahedron Lett. 2001, 42, 3525-3527;
33. c) D. Enders, A. A. Narine, F. Toulgoat, T. Bisschops, Angew. Chem. 2008, 120, 5744-5748;
34. Angew. Chem. Int. Ed. 2008, 47, 5661-5665.
35. a) N. Srivastava, B. K. Banik, J. Org. Chem. 2003, 68, 2109-2114;
36. b) D. Enders, S. Wallert, Synlett 2002, 304-306;
37. c) E. Vedejs, M. Gingras, J. Am. Chem. Soc. 1994, 116, 579-588;
38. d) G. Bartoli, M. Bosco, E. Marcantoni, M. Petrini, L. Sambri, E. Torregiani, J. Org. Chem. 2001, 66, 9052-9055.
39. a) Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328-9329;
40. b) H. Jiang, J. B. Nielsen, M. Nielsen, K. A. Jorgensen, Chem. Eur. J. 2007, 13, 9068-9075;
41. c) X. J. Lu, L. Deng, Angew. Chem. 2008, 120, 7824-7827;
42. Angew. Chem. Int. Ed. 2008, 47, 7710-7713.
43. a) D. Uraguchi, D. Nakashima, T. Ooi, J. Am. Chem. Soc. 2009, 131, 7242-1243;
44. b) V. Polshettiwar, R. S. Varma, Tetrahedron Lett. 2007, 48, 8735-8738.
45. C. Mukherjee, A. K. Misra, Lett. Org. Chem. 2007, 4, 54-59.
46. N. Vale, J. Matos, R. Moreira, P. Gomes, Tetrahedron 2008, 64, 11144-11149.
47. a) J. L. G. Ruano, V. Marcos, J. Aleman, Angew. Chem. 2009, 121, 3201-3203;
48. Angew. Chem. Int. Ed. 2009, 48, 3155-3157;
49. b) J.L.G. Ruano, M. A. Fernandez-Ibanez, J. A. Fernandez-Salas, M. C. Maestro, P. Marquez-Lopez, M. M. Rodriguez-Fernandez, J. Org. Chem. 2009, 74, 1200-1204;
50. c)P. Balbuena, E. M. Rubio, C.O. Mellet, J. M. G. Fernandez, Chem. Commun. 2006, 2610-2612.
51. Similar isomerization of diastereomers please see: A. R. Katritzky, H. Y. He, J. Wang, J. Org. Chem. 2002, 67, 4951-4956.
52. a) V. Jurkauskas, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 2892-2893;
53. b) A. Yamaguchi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 10842;
54. c) L. Borén, K. Leijondahl, J. E. Bäckvall, Tetrahedron Lett. 2009, 50, 3237-3240;
55. d) A.T. Parsons, J. S. Johnson, J. Am. Chem. Soc. 2009, 131, 3122;
56. for reviews, see: e) F. F. Huerta, A. B. E. Minidis, J. E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321-331;
57. f) A. H. Kamaruddin, M. H. Uzir, H. Y. Aboul-Enein, H. N. A. Halim, Chirality 2009, 21, 449-467;
58. g) J. Steinreiber, K. Faber, H. Griengl, Chem. Eur. J. 2008, 14, 8060-8072.
59. D. Seebach, B. Lamatsch, R. Amstutz, A. K. Beck, M. Dobler, M. Egli, R. Fitzi, M. Gautschi, B. Herradon, P. C. Hidber, J. J. Irwin, R. Locher, M. Maestro, T. Maetzke, A. Mourino, E. Pfammatter, D. A. Plattner, C. Schickli, W. B. Schweizer, P. Seiler, G. Stucky, W. Petter, J. Escalante, E. Juaristi, D. Quintana, C. Miravitlles, E. Molins, Helv. Chim. Acta 1992, 75, 913-934.
60. a) D. .Enders, M. R. M. Huttl, C. Grondai, G. Raabe, Nature 2006, 441, 861-863;
61. b) H. Liu, G. Dagousset, G. Masson, P. Retailleau, X P. Zhu, J. Am. Chem. Soc. 2009, 131, 4598-4599;
62. c) W. Zhu, M. Mena, E. Jnoff, N. Sun, P. Pasau, L. Ghosez, Angew. Chem. 2009, 121, 5994-5997;
63. Angew. Chem. Int. Ed. 2009, 48, 5880-5883;
64. for reviews, see: d) D. J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628-1661;
65. Angew. Chem. Int. Ed. 2005, 44, 1602-1634;
66. e)B.B. Toure, D. G. Hall, Chem. Rev. 2009, 109, 4439-4486;
67. f) B. Ganem, Acc. Chem. Res. 2009, 42, 463-472;
68. g) D. Enders, C. Grondai, M. R. M. Huttl, Angew. Chem. 2007, 119, 1590-1601.;
69. Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
70. h) J. D. Sunderhaus, S. F. Martin, Chem. Eur. J. 2009, 15, 1300-1308.