Optically pure trans-2,3-disubstituted N-sulfinyl aziridines. Regio- and stereoselective opening mediated by the sulfinyl group

Tetrahedron

Volumn 62, Issue 36, 2006, Pages 8525-8532

  Arroyo, Yolanda ^a   Meana, Ángela ^a   Rodríguez, J Félix ^a   Santos, Mercedes ^a   Sanz Tejedor, M Ascensión ^a   García Ruano, José L ^b  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; NITROGEN; SULFONAMIDE; SULFONIUM DERIVATIVE;

ARTICLE; ATOM; CHROMATOGRAPHY; DRUG SYNTHESIS; HYDROGENOLYSIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY; SUBSTITUTION REACTION; TRANS ISOMER;

EID: 33746555945     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.072     Document Type: Article

References (69)

1. For reviews on this subject see:
2. Tanner D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599-619
3. Pearson W.H., Lian B.W., and Bergmeier S.C. In: Katrytzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 1A (1966), Pergamon, New York, NY 1-60
4. Ibuka T. Chem. Soc. Rev. 27 (1998) 145-154
5. Stamrn H. J. Prakt. Chem. 341 (1999) 319-331
6. Atkinson R.S. Tetrahedron 55 (1999) 1519-1559
7. McCoull W., and Davis F.A. Synthesis (2000) 1347-1365
8. Sweeney J.B. Chem. Soc. Rev. 31 (2002) 247-258
9. Hu X.E. Tetrahedron 60 (2004) 2701-2743
10. Kasai M., and Kono M. Synlett (1992) 778-790
11. Remers W.A., and Dorr R.T. In: Peletier W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 6 (1988), Wiley, New York, NY 1
12. Shi M., Jiang J.-K., and Feng Y.S. Tetrahedron: Asymmetry 11 (2000) 4923-4933
13. Ekegren J.K., Roth P., Källström K., Tarnai T., and Andersson P.G. Org. Biomol. Chem. 1 (2003) 358-366
14. Hou X.-Y., Xu C.-L., Liu L.-T., Li G.-L., and Wang D.K. Synthesis (2005) 3620-3626
15. For recent reviews in the asymmetric synthesis of aziridines see:
16. Osborn H.M.I., and Sweeney J. Tetrahedron: Asymmetry 8 (1997) 1693-1715
17. Li A.-H., Dai L.-X., and Aggarwal V.K. Chem. Rev. 97 (1997) 2341-2372
18. Müller P., and Fruit C. Chem. Rev. 103 (2003) 2905-2919 See also Refs. 1a and 1f
19. Evans D.A., Faul M.M., Bilodeau M.T., Andersson B.A., and Barnes P.A. J. Am. Chem. Soc. 115 (1993) 5328-5329
20. Li Z., Conser K.R., and Jacobsen E.N. J. Am. Chem. Soc. 115 (1993) 5326-5327
21. Sander C.J., Gillepsie K.M., Bell D., and Scott P. J. Am. Chem. Soc. 122 (2000) 7131-7133
22. Gillepsie K.M., Sanders C.J., O'Shaughnessy P., Westmoreland I., Thickitt C.P., and Scott P. J. Org. Chem. 67 (2002) 3450-3458
23. Xu J., Ma L., and Jiao P. Chem. Commun. (2004) 1616-1617
24. Kwong H.-L., Liu D., Chan K.-Y., Huang K.-H., and Che Ch.-M. Tetrahedron Lett. 45 (2004) 3965-3968
25. Hansen K.B., Finney N.S., and Jacobsen E.N. Angew. Chem., Int. Ed. Engl. 34 (1995) 676-678
26. Rasmussen K.G., and Jorgensen K.A. J. Chem. Soc., Chem. Commun. (1995) 1401-1402
27. Antilla J.C., and Wulff W.D. J. Am. Chem. Soc. 121 (1999) 5099-5100
28. Antilla J.C., and Wulff W.D. Angew. Chem., Int. Ed. 39 (2000) 4518-4521
29. Chemla F., and Ferreira F. J. Org. Chem. 69 (2004) 8244-8250
30. Davis F.A., Zhou P., and Reddy G.V. J. Org. Chem. 59 (1994) 3243-3245
31. Davis F.A., Liu H., and Reddy G.V. Tetrahedron Lett. 37 (1996) 5473-5476
32. Davis F.A., Liu H., Zhou P., Fang T.N., Reddy G.V., and Zhang Y.L. J. Org. Chem. 64 (1999) 7559-7567
33. Davis F.A., Ramachandar T., and Wu Y. J. Org. Chem. 68 (2003) 6894-6898
34. Davis F.A., Wu Y., Yan H., McCoull W., and Prasad K.R. J. Org. Chem. 68 (2003) 2410-2419
35. García-Ruano J.L., Fernández I., and Hamdouchi Ch. Tetrahedron Lett. 36 (1995) 295-298
36. García-Ruano J.L., Fernández I., Prado M., and Alcudia A. Tetrahedron: Asymmetry 7 (1996) 3407-3414
37. Davis F.A., Zhou P., Liang Ch.-H., and Reddy R.E. Tetrahedron: Asymmetry 6 (1995) 1511-1514
38. Morton D., Pearson D., Field R.A., and Stockman R.A. Synlett (2003) 1985-1988
39. Morton D., Pearson D., Field R.A., and Stockman A. Org. Lett. 6 (2004) 2377-2380
40. Fernández I., Valdivia V., Gori B., Alcudia F., Alvárez E., and Khiar N. Org. Lett. 7 (2005) 1307-1310
41. Zheng J.-C., Liao W.-W., Sun X.-X., Sun X.-L., Tang Y., Dai L.-X., and Deng J.-G.N. Org. Lett. 7 (2005) 5789-5792
42. Morton D., Pearson D., Field R.A., and Stockman A. Chem. Commun. (2006) 1833-1835
43. Li A.-H., Zhou Y.-G., Dai L.-X., Hou X.-L., Xia L.-J., and Lin L. J. Org. Chem. 63 (1998) 4338-4348
44. Solladié-Cavallo A., Roje M., Welter R., and Sunjic V. J. Org. Chem. 69 (2004) 1409-1412
45. Aggarwal V.K., Thomson A., Jones R.V.H., and Standen M.C.H. J. Org. Chem. 61 (1996) 8368-8369
46. Aggarwal V.K., Ferrara M., O'Brien C.J., Thomson A., Jones R.V.H., and Fieldhouse R. J. Chem. Soc., Perkin Trans. 1 (2001) 1635-1643
47. Aggarwal V.K., Alonso E., Fang G., Ferrara M., Hynd G., and Porcelloni M. Angew. Chem., Int. Ed. 40 (2001) 1433-1436
48. For a recent review see:. Fulton J.R., Aggarwal V.K., and Vicente J. Eur. J. Org. Chem. (2005) 1479-1492
49. Cantrill A.A., Hall L.D., Jarvis A.N., Osborn H.M.I., Raphy J., and Sweeney J.B. Chem. Commun. (1996) 7559-7560
50. McLaren A.B., and Sweeney J.B. Org. Lett. 1 (1999) 1339-1341
51. Sweeney J.B., Cantrill A.A., McLaren A.B., and Thobhani S. Tetrahedron 62 (2006) 3681-3693
52. Sweeney J.B., Cantrill A.A., Drew M.G.B., McLaren A.B., and Thobhani S. Tetrahedron 62 (2006) 3694-3703
53. Dahanukar I.A., and Zavialov I.A. Curr. Opin. Drug Discovery Dev. 5 (2002) 918-927
54. Kim S.K., and Jacobsen E.N. Angew. Chem., Int. Ed. 43 (2004) 3952-3954
55. García-Ruano J.L., Lorente A., and Rodríguez-Ramos J.H. Tetrahedron Lett. 39 (1998) 9765-9768
56. Arroyo Y., Meana A., Rodríguez J.F., Santos M., Sanz-Tejedor M.A., and García-Ruano J.L. J. Org. Chem. 70 (2005) 3914-3920
57. García-Ruano J.L., Martín Castro A.M., and Rodríguez Ramos J.H. Tetrahedron Lett. 37 (1996) 4569-4572
58. García-Ruano J.L., Fernández Ibañez M.A., Maestro M.C., and Rodríguez Fernández M.M. Tetrahedron 62 (2006) 1245-1252
59. Clayden J., Mitjans D., and Youssef L.H. J. Am. Chem. Soc. 124 (2002) 5266-5267
60. Liu B., and Shine H.J. J. Phys. Org. Chem. 14 (2001) 81-89
61. Aggarwal V.K., Charmant J.P.H., Ciampi C., Hornby J.M., O'Brien C.J., Hynd G., and Parsons R. J. Chem. Soc., Perkin Trans. 1 (2001) 3159-3166
62. Yang X.-F., Zhang M.-J., Hou X.-L., and Dai L.-X. J. Org. Chem. 67 (2002) 8097-8103
63. Khusainova N.G., Bredikhina Z.A., Ishmaeva E.A., Musina A.A., and Pudovick A.N. J. Gen. Chem., USSR 51 (1981) 526-529
64. Lohray B.B., and Ahujas J.R. J. Chem. Soc., Chem. Commun. (1991) 95-97
65. Reyes A., and Juaristi E. Chirality 10 (1998) 95-99
66. Shimizu M., Tsukamoto K., Matsutani T., and Fujisawa T. Tetrahedron 54 (1998) 10265-10274
67. Aminoalcohol 5a was obtained after purification by SCX from the crude reaction mixture.
68. García-Ruano J.L., and Aleman J. Org. Lett. 5 (2003) 4513-4516
69. Davis F.K., Reddy R.E., Szewczyk J.M., Reddy G.V., Portonovo P.S., Zhang H., Fanelli D., Reddy R.T., Zhou P., and Carrol P.J. J. Org. Chem. 62 (1997) 2555-2563