A new stereoselective synthesis of cyclopropanes containing quaternary stereocentres via organocatalytic michael addition to vinyl selenones

Advanced Synthesis and Catalysis

Volumn 351, Issue 11-12, 2009, Pages 1801-1806

  Marini, Francesca ^a   Sternativo, Silvia ^a   Del Verme, Francesca ^a   Testaferri, Lorenzo ^a   Tiecco, Marcello ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Asymmetric organocatalysis; Cyclopropanes; Michael addition; Quaternary stereocenters; Selenones

Indexed keywords

EID: 68949150954     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900222     Document Type: Article

References (70)

1. a) Small ring compounds in organic synthesis VI, in: Top. Curr. Chem. (Ed.: A. de Meijere), Springer, Berlin, 2000, vol. 207;
2. b) J. Salaun, Curr. Med. Chem. 1995, 2, 511;
3. c) W. A. Donaldson, Tetrahedron 2001, 57, 8589;
4. d) R. Faust, Angew. Chem. 2001, 113, 2312;
5. Angew. Chem. Int. Ed. 2001, 40, 2251;
6. e) A. Reichelt, S. F. Martin, Acc. Chem. Res. 2006, 39, 433.
7. For reviews on cyclopropanes as intermediates in organic synthesis see: a) H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151;
8. b) H. N. C. Wong, M. Y. Hon, C. W. Tse, Y. C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165;
9. c) M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117.
10. For recent reviews see: a) H. Pellissier Tetrahedron 2008, 64, 7041;
11. b) H. Lebel, J.-F. Marcoux, C. Molinaro, A.B. Charette, Chem. Rev. 2003, 103, 977;
12. c) R. C. Hartley, S. T. Caldwell, J. Chem. Soc. Perkin Trans. 1 2000, 477.
13. For some recent examples of asymmetric MIRC reactions see: a) C. C. C. Johansson, N. Bremeyer, S. V. Ley, D. R. Owen, S. C. Smith, M. J. Gaunt, Angew. Chem. 2006, 118, 6170;
14. Angew. Chem. Int. Ed. 2006, 45, 6024;
15. b) R. K. Kunz, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 3240;
16. c) S.H. McCooey, T. McCabe, S.J. Connon, J. Org. Chem. 2006, 71, 7494;
17. d) H. M. Hansen, D. A. Longbottom, S. V. Ley, Chem. Commun. 2006, 4838;
18. e) H. Xie, L. Zu, H. Li, J. Wang, W.J. Wang, J. Am. Chem. Soc. 2007, 129, 10886;
19. f) R. Rios, H. Sunden, J. Vesely, G.-L. Zhao, P. Dziedzic, A. Cordova, Adv. Synth. Catal. 2007, 349, 1028;
20. g) A. Hartikka, A. T. Slosarczyk, P. I. Arvidsson, Tetrahedron: Asymmetry 2007, 18, 1403;
21. h) J. Vesely, G.-L. Zhao, A. Bartoszewicz, A. Cordova, Tetrahedron Lett. 2008, 49, 4209;
22. i) V. Wascholowski, H. M. Hansen, D. A. Longbottom, S. V. Ley, Synthesis 2008, 1269;
23. j) I. Ibrahem, G.-L. Zhao, R. Rios, J. Vesely, H. Sunden, P. Dziedzic, A. Cordova, Chem. Eur. J. 2008, 14, 7867;
24. k) J. Lv, J. Zhang, Z. Lin, Y. Wang, Chem. Eur. J. 2009, 15, 972;
25. l) Y. Xuan, S. Nie, L. Dong, J. Zhang, M. Yan, Org. Lett. 2009, 11, 1583.
26. F. Marini, S. Sternativo, F. Del Verme, L. Testaferri, M. Tiecco, Adv. Synth. Catal. 2009, 351, 103.
27. a) M. Tiecco, A. Carlone, S. Sternativo, F. Marini, G. Bartoli, P. Melchiorre, Angew. Chem. 2007, 119, 7006;
28. Angew. Chem. Int. Ed. 2007, 46, 6882;
29. b) M. Tiecco, L. Testaferri, A. Temperini, R. Terlizzi, L. Bagnoli, F. Marini, C. Santi, Org. Biomol. Chem, 2007, 5, 3510;
30. c) M. Tiecco, L. Testaferri, L. Bagnoli, G. Scarponi, A. Temperini, F. Marini, C. Santi, Tetrahedron: Asymmetry 2007, 18, 2758;
31. d) M. Tiecco, L. Testaferri, A. Temperini, L. Bagnoli, F. Marini, C. Santi, Chem. Eur. J. 2004, 10, 1752;
32. e) V. R. Ward, M. A. Cooper, A. D. Ward, J. Chem. Soc. Perkin Trans. 1 2001, 944;
33. f) M. A. Cooper, A. D. Ward, Aust. J. Chem. 1997, 50, 181;
34. g) A. Toshimitsu, C. Hirosawa, S. Tanimoto, S. Uemura, Tetrahedron Lett. 1992, 33, 4017;
35. h) A. Krief, W. Dumont, J.-N. Denis, J. Chem. Soc. Chem. Commun. 1985, 571;
36. i) A. Krief, W. Dumont, A. F. De Mahieu, Tetrahedron Lett. 1988, 29, 3269;
37. j) M. Tiecco, D. Chianelli, L. Testaferri, M. Tingoli, D. Bartoli, Tetrahedron 1986, 42, 4889;
38. k) M. Tiecco, D. Chianelli, L. Testaferri, M. Tingoli, D. Bartoli, Tetrahedron 1986, 42, 4897;
39. l) I. Kuwajima R. Ando, T. Sugawara, Tetrahedron Lett. 1983, 24, 4429;
40. m) R. Ando, T. Sugawara, M. Shimizu, I. Kuwajima, Bull. Chem. Soc. Jpn. 1984, 57, 2897;
41. n) selenonium groups can also be easily displaced by nucleophiles. This property has been employed to develop a one-pot cyclopropanation reaction starting from vinylselenonium salts:
42. o) Y. Watanabe; Y. Ueno, T. Toru, Bull. Chem. Soc. Jpn. 1993, 66, 2042.
43. Vinyl selenones are prepared by oxidation of the corresponding selenides (see Supporting Information). For an update review on the synthesis of vinyl selenides see: G. Perin, E. J. Lenardao, R. G. Jacob, R. B. Panatieri, Chem. Rev. 2009, 109, 1277.
44. a) J. R. Denton, H. M. L. Davies, Org. Lett. 2009, 11, 787;
45. b) H. M. L. Davies, G. H. Lee, Org. Lett. 2004, 6, 2117.
46. a) J. R. Denton, K. Cheng, H. M. L. Davies Chem. Commun. 2008, 1238;
47. b) S. Arai, K. Nakayama, T. Ishida, T. Shioiri, Tetrahedron Lett. 1999, 40, 4215.
48. a) A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713;
49. b) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550;
50. Angew. Chem. Int. Ed. 2006, 45, 1520;
51. c) S. J. Connon, Chem. Eur. J. 2006, 12, 5418;
52. d) S. J. Connon, Chem. Commun. 2008, 2499;
53. e) S. J. Connon Synlett 2009, 354.
54. 2 and that the phenyl (E)-2-phenylethenyl sulfone is not reactive. See: H. Li, J. Song, L. Deng Tetrahedron 2009, 65, 3139. We tested one of the Deng's C6′-OH Cinchona alkaloid catalysts on 3A obtaining the adducts 4a/5a in low yield and poor diastereo- and enantioselectivity.
55. For Cinchona alkaloids-catalyzed asymmetric conjugate addition of carbon nucleophiles to β-unsubstituted vinyl sulfones see: a) T.-Y. Liu, J. Long, B.-J. Li, L. Jiang, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2006, 4, 2097;
56. b) H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948.
57. a) A. P. Krapcho, Synthesis 1982, 805;
58. b) A. P. Krapcho, Synthesis 1982, 893.
59. C. Cheng, H. Lu, F. Lee, Eur. J. Med Chem. 1991, 26, 125.
60. [15a]). The absolute configuration was assigned as 1S,2S by its (-) optical rotation typical for the (25)-isomers of 2-phenyl substituted cyclopropanecarboxylic derivatives. See: a) W. von E. Doering, L. R. Robertson, E. E. Ewing, J. Org. Chem. 1983, 48, 4280;
61. b) A. B. Chmurny, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 4237.
62. 1H NMR spectrum and specific optical rotation, respectively, with those reported in the literature. See: T. Kusumoto, A. Nakayama, K. Sato, T. Hiyama, S. Takehara, T. Shoji, M. Osawa, T. Kuriyama, K. Nakamura, T. Fujisawa, Tetrahedron Lett. 1991, 32, 939.
63. a) S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525;
64. Angew. Chem. Int. Ed. 2005, 44, 6367;
65. b) J. Wang, H. Li, L. Zu, W Jiang, H. Xie, W Duan, W. Wang, J. Am. Chem. Soc. 2006, 128, 12652;
66. c) C. Gu, L. Liu, Y. Sui, J.-L. Zhao, D. Wang, Y.-J. Chen, Tetrahedron: Asymmetry 2007, 18, 455.
67. [6j,l,m] The organocatalytic version of this process merits investigations. These are currently under way in our laboratory.
68. [6j]), the (E)-vinyl selenones 3A-F were prepared from the corresponding commercial or easily available vinyl bromides. See: a) H.-W You,. K.-J. Lee Synlett 2001 105;
69. b) C. Kuang, H. Senboku, M. Tokuda, Tetrahedron 2005, 61, 637.
70. The vinyl selenide precursor of the (E)-vinyl selenone 3G was prepared from commercial 1-octene and PhSeBr following a literature procedure: S. Raucher, M. R. Hansen, M. A. Colter, J. Org. Chem. 1978, 43, 4885.