Iron-catalyzed sulfonylimine synthesis under neutral conditions

Tetrahedron

Volumn 65, Issue 36, 2009, Pages 7380-7384

  Wu, Xiao Feng ^a   Vovard Le Bray, Chloé ^a   Bechki, Lazhar ^a   Darcel, Christophe ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BENZALDEHYDE; FERRIC CHLORIDE; IMINE; LEWIS ACID; N TOSYLBENZYLIMINE; NUCLEOPHILE; SULFANILAMIDE; SULFONYLIMINE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; POLYMERIZATION; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 67949092984     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.07.029     Document Type: Article

References (95)

1. For selected examples, see:
2. Bégué J.P., Bonnet-Delpon D., Crousse B., and Legros J. Chem. Soc. Rev. 34 (2005) 562-572
3. Gohain M. Synlett (2003) 2097-2098
4. Shim J.-G., and Yamamoto Y. Heterocycles 52 (2000) 885-895
5. Prakash G.K.S., Mandal M., and Olah G.A. Synlett (2001) 77-78
6. Bloch R. Chem. Rev. 98 (1998) 1407-1438
7. Weinreb S.M. Top. Curr. Chem. 190 (1997) 131-184
8. Davies F.A., Reddy R.T., and Weismiller M.C. J. Am. Chem. Soc. 111 (1989) 5964-5965
9. For selected examples:
10. Ooi T., Uematsu Y., and Maruoka K. J. Am. Chem. Soc. 128 (2006) 2548-2549
11. Duan H.F., Jia Y.X., Wang L.X., and Zhou Q.L. Org. Lett. 8 (2006) 2567-2569
12. Fujisawa H., Takahashi E., and Mukaiyama T. Chem.-Eur. J. 12 (2006) 5082-5093
13. Shi M., Chen L.-H., and Li C.-Q. J. Am. Chem. Soc. 127 (2005) 3790-3800
14. Soeta T., Kuriyama M., and Tomioka K. J. Org. Chem. 70 (2005) 297-300
15. Hayashi T., Kawai M., and Tokunaga N. Angew. Chem., Int. Ed. 43 (2004) 6125-6128
16. Yim H.K., and Wong H.N.C. J. Org. Chem. 69 (2004) 2892-2895
17. Wipf P., Kendall, and Stephenson C.R.J. J. Am. Chem. Soc. 125 (2003) 761-768
18. Yamada K.-I., Fujihara H., Yamamoto Y., Miwa Y., Taga T., and Tomioka K. Org. Lett. 4 (2002) 3509-3511
19. Wang D.K., Zhou Y.G., Tang Y., Hou X.-L., and Dai L.-X. J. Org. Chem. 64 (1999) 4233-4237
20. For selected examples:
21. Garcia-Mancheno O., Gomez-Arrayas R., and Carretero J.C. J. Am. Chem. Soc. 126 (2004) 456-457
22. Morgan P.E., McCague R., and Whiting A. J. Chem. Soc., Perkin Trans. 1 (2000) 515-525
23. Yao S., Johannsen M., Hazell R.G., and Jorgensen K.A. Angew. Chem., Int. Ed. 37 (1998) 3121-3124
24. Bauer T., Szymanski S., Jezewski A., Gluzinski P., and Jurczak J. Tetrahedron: Asymmetry 8 (1997) 2619-2625
25. Boger D.L., Corbett W.L., Curran T.T., and Kasper A.M. J. Am. Chem. Soc. 113 (1991) 1713-1729
26. Boger D.L., and Curran T.T. J. Org. Chem. 55 (1990) 5439-5442
27. Sisko J., and Weireb S.M. Tetrahedron Lett. 30 (1989) 3037-3040
28. Yamanaka M., Nishida A., and Nakagawa M. Org. Lett. 2 (2000) 159-161
29. Melnick M.J., Freyer A.J., and Weinreb S.M. Tetrahedron Lett. 29 (1988) 3891-3894
30. Taschaen D.M., Turos E., and Weinreb S.M. J. Org. Chem. 49 (1984) 5058-5064
31. Arini L.G., Sinclair A., Szeto P., and Stockman R.A. Tetrahedron Lett. 45 (2004) 1589-1591
32. Aggarwal V.K., Alonso E., Ferrara M., and Spey S.E. J. Org. Chem. 67 (2002) 2335-2344
33. Hori R., Aoyama T., and Shioiri T. Tetrahedron Lett. 41 (2000) 9455-9458
34. Wang D.-K., Dai L.-X., and Hou X.-L. Chem. Commun. (1997) 1231-1232
35. Li A.-H., Dai L.-X., Hou X.-L., and Chen M.-B. J. Org. Chem. 61 (1996) 4641-4648
36. Li A.-H., Dai L.-X., and Hou X.-L. Chem. Commun. (1996) 491-492
37. Davis F.A., ThimmaReddy R., and Reddy R.E. J. Org. Chem. 57 (1992) 6387-6389
38. Vishwakarma L.C., Stringer O.D., and Davis F.A. Org. Synth. 66 (1988) 203-210
39. For a review, see:. Weinreb S.M. Top. Curr. Chem. 190 (1997) 131-184
40. For selected examples, see:
41. Wynne J.H., Price S.E., Rorer J.R., and Stalick W.M. Synth. Commun. 33 (2003) 341-352
42. Jennings W.B., and Lovely C.J. Tetrahedron 47 (1991) 5561-5568
43. Boger D.L., Corbett W.L., Curran T.T., and Kasper A.M. J. Am. Chem. Soc. 113 (1991) 1713-1729
44. Jennings W.B., and Lovely C.J. Tetrahedron Lett. 29 (1988) 3725-3728
45. McKay W.R., and Proctor G.C. J. Chem. Soc., Perkin Trans. 1 (1981) 2435-2442
46. Lichtenberger J., Fleury S., and Barette B. Bull. Soc. Chim. Fr. (1955) 669-680
47. Boger D.L., and Corbett W.L. J. Org. Chem. 57 (1992) 4777-4780
48. Trost B.M., and Marrs C. J. Org. Chem. 56 (1991) 6468-6470
49. Georg G.I., Harriman G.C.B., and Peterson S.A. J. Org. Chem. 60 (1995) 7366-7368
50. For selected examples, see:
51. Khalafi-Nezhad A., Parhami A., Zare A., Nasrolahi-Shirazi A., Zare A.R.M., and Hassanirejad A. Can. J. Chem. 86 (2008) 456-461
52. Fan R., Pu D., Wen F., Ye Y., and Wang X. J. Org. Chem. 73 (2008) 3623-3625
53. Li Z., Ren X., Wei P., Wan H., Shi Y., and Ouyang P. Green Chem. 8 (2006) 433-436
54. Jain S.L., Sharma V.B., and Sain B. J. Mol. Catal. 239 (2005) 92-95
55. Garcia Ruano J.L., Aleman J., Cid M.B., and Parra A. Org. Lett. 7 (2005) 179-182
56. Lee K.Y., Lee C.G., and Kim J.N. Tetrahedron Lett. 44 (2003) 1231-1234
57. Jin T., Feng G., Yang M., and Li T. Synth. Commun. 34 (2004) 1277-1283
58. Chemla F., Hebbe V., and Normant J.-F. Synthesis (2000) 75-77
59. Love B.E., Raje P.S., and William II T.C. Synlett (1994) 493-494
60. Love B.E., and Ren J. J. Org. Chem. 58 (1993) 5556-5557
61. Boger D.L., Corbett W.L., Curran T.T., and Kasper A.M. J. Am. Chem. Soc. 113 (1991) 1713-1729
62. Vishwakarma L.C., Stringer O.D., and Davis F.A. Org. Synth. 66 (1988) 203-210
63. For complete reviews of the state of the art, see:
64. Bolm C., Legros J., Le Paih J., and Zani L. Chem. Rev. 104 (2004) 6217-6254
65. Cahiez G., and Marquais S. Pure Appl. Chem. 68 (1996) 53-60
66. Sherry B.D., and Fürstner A. Acc. Chem. Res. 41 (2008) 1500-1511
67. Tondreau A.M., Lobkovsky E., and Chirik P.J. Org. Lett. 10 (2008) 2789-2792
68. Shaikh N.S., Enthaler S., Junge K., and Beller M. Angew. Chem., Int. Ed. 47 (2008) 2497-2501
69. Gelalcha F.G., Bitterlich B., Anilkumar G., Tse M.K., and Beller M. Angew. Chem., Int. Ed. 46 (2007) 7293-7296
70. Shaikh N.S., Junge K., and Beller M. Org. Lett. 9 (2007) 5429-5432
71. Nishiyama H., and Furuta A. Chem. Commun. (2007) 760-762
72. Furuta A., and Nishiyama H. Tetrahedron Lett. 49 (2007) 110-113
73. Shi F., Tse M.K., Li Z., and Beller M. Chem.-Eur. J. 14 (2008) 8793-8797
74. Nakanishi M., and Bolm C. Adv. Synth. Catal. 349 (2007) 861-864
75. Pavan C., Legros J., and Bolm C. Adv. Synth. Catal. 347 (2005) 703-705
76. Pavan C., Legros J., and Bolm C. Adv. Synth. Catal. 347 (2005) 703-705
77. Legros J., and Bolm C. Chem.-Eur. J. 11 (2005) 1086-1092
78. Legros J., and Bolm C. Angew. Chem., Int. Ed 43 (2004) 4225-4228
79. Legros J., and Bolm C. Angew. Chem., Int. Ed. 42 (2003) 5487-5489
80. Bitterlich B., Schroeder K., Tse M.K., and Beller M. Eur. J. Org. Chem. 29 (2008) 4867-4870
81. Gelalcha F.G., Anilkumar G., Tse M.K., Bruckner A., and Beller M. Chem.-Eur. J. 14 (2008) 7687-7698
82. Gelalcha F.G., Bitterlich B., Anilkumar G., Tse M.K., and Beller M. Angew. Chem., Int. Ed. 46 (2007) 7293-7296
83. Schroeder K., Tong X., Bitterlich B., Tse M.K., Gelalcha F.G., Brueckner A., and Beller M. Tetrahedron Lett. 48 (2007) 6339-6342
84. Bitterlich B., Anilkumar G., Gelalcha F.G., Spilker B., Grotevendt A., Jackstell R., Tse M.K., and Beller M. Chem. Asian J. 2 (2007) 521-529
85. Anilkumar G., Bitterlich B., Gelalcha F.G., Tse M.K., and Beller M. Chem. Commun. (2007) 289-291
86. Gaillard S., and Renaud J.-L. ChemSusChem 1 (2008) 505-509
87. Enthaler S., Hagemann B., Erre G., Junge K., and Beller M. Chem. Asian J. 1 (2006) 598-604
88. Bart S.C., Lobkovsky E., and Chirik P.J. J. Am. Chem. Soc. 126 (2004) 13794-13807
89. Wu X.-F., and Darcel C. Eur. J. Org. Chem. (2009) 1144-1147
90. Wu X.-F., Bezier D., and Darcel C. Adv. Synth. Catal. 351 (2009) 367-370
91. Ladépêche A., Tam E., Ancel J.-E., and Ghosez L. Synthesis (2004) 1375-1380
92. Hayashi T., and Ishigedani M. J. Am. Chem. Soc. 122 (2000) 976-977
93. Vass A., Dudas J., and Varma R.S. Tetrahedron Lett. 40 (1999) 4951-4954
94. Williams D.R., Robinson L.A., Amato G.S., and Osterhout M.H. J. Org. Chem. 57 (1992) 3740-3744
95. Sharghi H., Hosseini-Sarvari M., and Ebrahimpourmo-ghaddam S. ARKIVOC xv (2007) 255-264