Synthesis of enantiopure 1,4-dioxanes, morpholines, and piperazines from the reaction of chiral 1,2-diols, amino alcohols, and diamines with vinyl selenones

Chemistry - A European Journal

Volumn 17, Issue 3, 2011, Pages 993-999

  Bagnoli, Luana ^a   Scarponi, Catalina ^a   Rossi, Maria Giovanna ^a   Testaferri, Lorenzo ^a   Tiecco, Marcello ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

cyclization; enantioselectivity; Michael addition; oxygen heterocycles; selenium

Indexed keywords

AMINO ALCOHOLS; ENANTIOPURE; HETEROCYCLES; MICHAEL ADDITION; MORPHOLINES; NOVEL APPLICATIONS; ONE POT; OXYGEN HETEROCYCLES; PHARMACEUTICAL COMPOUNDS; RING-CLOSURE; SELENONES;

ADDITION REACTIONS; ALCOHOLS; ENANTIOSELECTIVITY; ETHERS; OXYGEN; SELENIUM; SYNTHESIS (CHEMICAL);

CYCLIZATION;

1,4-DIOXANE; AMINOALCOHOL; DIAMINE; DIOXANE; DIOXANE DERIVATIVE; MORPHOLINE DERIVATIVE; PIPERAZINE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ALCOHOLS; DIAMINES; DIOXANES; MOLECULAR STRUCTURE; MORPHOLINES; PIPERAZINES; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 78651452043     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002593     Document Type: Article

References (63)

1. J. M. Concellõn, P. L. Bernard, V. delSolar, S. Garcia-Granda, M.-R. Diaz, Adv. Synth. Catal. 2008, 350, 477-481 and references cited therein
2. M. C. Wilkinson, R. Bell, R. Landon, P. O. Nikiforov, A. J. Walzer, Synlett 2006, 2151-2153
3. M. Tiecco, L. Testaferri, F. Marini, S. Sternativo, C. Santi, L. Bagnoli, A. Temperini, Tetrahedron: Asymmetry 2003, 14, 1095-1102
4. H. Fujioka, N. Matsunaga, H. Kitagawa, Y. Nagatomi, M. Kondo, Y. Kita, Tetrahedron: Asymmetry 1995, 6, 2117-2120
5. K. S. Kim, J. Park II, P. Ding, Tetrahedron Lett. 1998, 39, 6471-6474.
6. For morpholines, see R. Wijtmans, M. K. S. Vink, H. E. Schoemaker, F. L. vanDelft, R. H. Blaauw, F. P. J. T. Rutjes, Synthesis 2004, 641-662
7. M. Breuning, M. Winnacker, M. Steiner, Eur. J. Org. Chem. 2007, 2100-2106
8. B. A. Lanman, A. G. Myers, Org. Lett. 2004, 6, 1045-1047
9. M. D'hooghe, T. Vanlanangendonck, K. W. Tornroos, N. J. DeKimpe, J. Org. Chem. 2006, 71, 4678-4681; for the piperazines and thiomorpholines, see
10. D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 2003, 103, 893-930
11. J. Mirzaei, F. Siavoshi, S. Emami, F. Safari, M. R. Khoshayand, A. Shafiee, A. Foroumadi, Eur. J. Med. Chem. 2008, 43, 1575-1580
12. M. Biava, G. C. Porretta, D. Deidda, R. Pompei, A. Tafi, F. Manetti, Bioorg. Med. Chem. 2003, 11, 515-520
13. C. H. Oh, S. C. Lee, K. S. Lee, E. R. Woo, C. Y. Hong, B.-S. Yang, D. J. Baek, J.-H. Cho, Arch. Pharm. Med. Chem. 1999, 332, 187-190
14. J. Morris, D. G. Wishka, W. R. Humphrey, A. H. Lin, A. L. Witse, C. W. Benjamin, R. R. Gorman, R. J. Shebuski, Bioorg. Med. Chem. Lett. 1994, 4, 2621-2626.
15. D. Albanese, D. Landini, M. Penso, A. Tagliabue, E. Carlini, Org. Process Res. Dev. 2010, 14, 705-711
16. R. Dave, N. A. Sasaki, Tetrahedron: Asymmetry 2006, 17, 388-401.
17. M. Tiecco, L. Testaferri, F. Marini, S. Sternativo, C. Santi, L. Bagnoli, A. Temperini, Tetrahedron: Asymmetry 2003, 14, 2651-2657
18. R. Pedrosa, C. Andres, P. Mendiguchia, J. Nieto, J. Org. Chem. 2006, 71, 8854-8863
19. E. Brenner, R. M. Baldwin, G. Tamagnan, Org. Lett. 2005, 7, 937-939
20. M. L. Leathen, B. R. Rosen, J. P. Wolfe, J. Org. Chem. 2009, 74, 5107-5110
21. V. Lupi, D. Albanese, D. Landini, D. Scaletti, M. Penso, Tetrahedron 2004, 60, 11709-11718
22. J. Nonnenmacher, F. Grellepois, C. Portella, Eur. J. Org. Chem. 2009, 3726-3731
23. M. Berkheij, L. vanderSluis, C. Sewing, D. J. den Boer, J. W. Terpstra, H. Hiemstra, W. I. I. Bakker, A. vandenHoogenband, J. H. vanMaarseveen, Tetrahedron Lett. 2005, 46, 2369-2371
24. K. Rossen, P. J. Pye, L. M. DiMichele, R. P. Volante, P. J. Reiderh, Tetrahedron Lett. 1998, 39, 6823-6826.
25. C. Kashima, K. Harada, J. Chem. Soc., Perkin Trans. 1 1988, 1521-1526
26. U. Bhatt, G. Just, Helv. Chim. Acta 2000, 83, 722-727
27. P. H. Liang, L. W. Hsin C. Y. Cheng, Bioorg. Med. Chem. 2002, 10, 3267-3276.
28. M. Yar, E. M. McGarrigle, V. K. Aggarwal, Angew. Chem. 2008, 120, 3844-3846
29. Angew. Chem. Int. Ed. 2008, 47, 3784-3786
30. M. Yar, E. McGarrigle, V. K. Aggarwal, Org. Lett. 2009, 11, 257-260.
31. A. Krief, W. Dumont, J.-N. Denis, J. Chem. Soc. Chem. Commun. 1985, 571-572
32. M. A. Cooper, A. D. Ward, Aust. J. Chem. 1997, 50, 181-187
33. M. A. Cooper, A. D. Ward, Tetrahedron Lett. 1994, 35, 5065-5068
34. M. Tiecco, L. Testaferri, L. Bagnoli, C. Scarponi, A. Temperini, F. Marini, C. Santi, Tetrahedron: Asymmetry 2007, 18, 2758-2767.
35. A. Toshimitsu, H. Fuji, Chem. Lett. 1992, 2017-2018
36. A. Toshimitsu, C. Hirosawa, S. Tanimoto, S. Uemura, Tetrahedron Lett. 1992, 33, 4017-4020
37. M. Tiecco, L. Testaferri, A. Temperini, L. Bagnoli, F. Marini, C. Santi, Chem. Eur. J. 2004, 10, 1752-1764
38. M. Tiecco, L. Testaferri, A. Temperini, R. Terlizzi, L. Bagnoli, F. Marini, C. Santi, Org. Biomol. Chem. 2007, 5, 3510-3519.
39. A. Toshimitsu, S. Uemura, in Organoselenium Chemistry: A Pratical Approach (Ed.:, T.G. Back,), Oxford University Press, New York, 1999, pp. 241-256.
40. C.-Y. Zhu, X.-Y. Cao, B.-H. Zhu, C. Deng, X.-L. Sun, B.-Q. Wang, Q. Shen, Y. Tang, Chem. Eur. J. 2009, 15, 11465-11468
41. X.-M. Deng, P. Cai, S. Ye, X. L. Sun, W.-W. Liao, K. Li, Y. Tang, Y.- D. Wu, L.-X. Dai, J. Am. Chem. Soc. 2006, 128, 9730-9740
42. J.-F. Brière, P. Metzner, Organosulfur Chem. Asymmetric Synth. 2008, 179-208
43. H. Pellissier, Tetrahedron 2008, 64, 7041-7095
44. H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050.
45. H.-Y. Wang, F. Yang, X.-L. Li, X.-M. Yan, Z.-Z. Huang, Chem. Eur. J. 2009, 15, 3784-3789
46. Y. Watanabe, Y. Ueno, T. Toru, Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047.
47. M. Shimizu, R. Ando, I. Kuwajima, J. Org. Chem. 1984, 49, 1230-1238
48. M. Shimizu, I. Kuwajima, J. Org. Chem. 1980, 45, 4063-4065
49. M. Tiecco, D. Chianelli, L. Testaferri, M. Tingoli, D. Bartoli, Tetrahedron 1986, 42, 4889-4896
50. M. Tiecco, D. Chianelli, M. Tingoli, L. Testaferri, D. Bartoli, Tetrahedron 1986, 42, 4897-4906.
51. L. Bagnoli, C. Scarponi, L. Testaferri, M. Tiecco, Tetrahedron: Asymmetry 2009, 20, 1506-1514.
52. F. Marini, S. Sternativo, F. delVerme, L. Testaferri, M. Tiecco, Adv. Synth. Catal. 2009, 351, 1801-1806.
53. H. Hagiwara, H. Sakai, M. Kirita, T. Hoshi, T. Suzuki, M. Ando, Tetrahedron 2000, 56, 1445-1449.
54. M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli, M. Montanucci, Tetrahedron Lett. 1984, 25, 4975-4978
55. L. Testaferri, M. Tiecco, M. Tingoli, D. Chianelli, Tetrahedron 1985, 41, 1401-1408.
56. S. Raucher, M. R. Hansen, M. A. Colter, J. Org. Chem. 1978, 43, 4885-4887.
57. L. A. Gandon, A. G. Russell, T. Gveli, A. E. Brodwolf, B. M. Kariuki, N. Spencer, J. S. Snaith, J. Org. Chem. 2006, 71, 5198-5207.
58. J. L. Vicario, D. Badia, L. Carrillo, Arkivoc 2007, iv, 304-311.
59. G. Bettoni, C. Franchini, R. Perrone, V. Tortorella, Tetrahedron 1980, 36, 409-415.
60. The coupling constants of the H-5 proton of compound 14 d were calculated after spin decoupling by irradiating H-6. The signal of H-5 then appeared as a doublet with J=10Hz.
61. L. Costantino, D. Barlocco, Curr. Med. Chem. 2006, 13, 65-85.
62. J. Szymoniak, J. Besançon, C. Moïse, Tetrahedron 1992, 48, 3867-3876.
63. L. L. Santos, V. R. Ruiz, M. J. Sabater, A. Corma, Tetrahedron 2008, 64, 7902-7909.