Oxidative tandem alkoxide conjugate addition to nitroalkenes/radical 5-exo cyclizations - A versatile synthesis of functionalized 3-nitrotetrahydrofurans

Tetrahedron

Volumn 68, Issue 5, 2012, Pages 1521-1539

  Jahn, Ullrich ^a   Rudakov, Dmytro ^b   Jones, Peter G ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Electron transfer; Oxidation; Radicals; Tandem reaction; Tetrahydrofurans

Indexed keywords

ALKENE DERIVATIVE; ALKYL GROUP; ALLYL COMPOUND; COPPER DERIVATIVE; HALIDE; HALOGEN; LIGAND; LITHIUM DERIVATIVE; NITRO DERIVATIVE; OXIDE; OXIDIZING AGENT; RADICAL; SOLVENT; TETRAHYDROFURAN DERIVATIVE;

ADDITION REACTION; ARTICLE; CONJUGATION; CYCLIZATION; DIASTEREOISOMER; MODEL; OXIDATION; PRIORITY JOURNAL; PROTON TRANSPORT; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84855602662     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.12.010     Document Type: Article

References (108)

1. L.F. Tietze, G. Brasche, and K. Gericke Domino Reactions in Organic Synthesis 2006 Wiley-VCH Weinheim
2. K.C. Nicolaou, D.J. Edmonds, and P.G. Bulger Angew. Chem., Int. Ed. 45 2006 7134 7186
3. L.F. Tietze Chem. Rev. 96 1996 115 136
4. Selected Reviews: C.J. Chapman, and C.G. Frost Synthesis 2007 1 21
5. G. Balme, D. Bouyssi, and N. Monteiro Top. Organomet. Chem. 19 2006 115 148
6. V. Dragutan, and I. Dragutan J. Organomet. Chem. 691 2006 5129 5147
7. A. de Meijere, P. von Zezschwitz, and S. Bräse Acc. Chem. Res. 38 2005 413 422
8. A. Ajamian, and J.L. Gleason Angew. Chem., Int. Ed. 43 2004 3754 3760
9. G.V. Garcia, and N.S. Nudelman Org. Prep. Proced. Int. 35 2003 445 500
10. A. de Meijere, P. von Zezschwitz, H. Nüske, and B. Stulgies J. Organomet. Chem. 653 2002 129 140
11. J. Rodriguez Synlett 1999 505 518
12. H.-C. Guo, and J.-A. Ma Angew. Chem., Int. Ed. 45 2006 354 366
13. G. Poli, G. Giambastiani, and A. Heumann Tetrahedron 56 2000 5959 5989
14. S.-I. Ikeda Acc. Chem. Res. 33 2000 511 519
15. General reviews: M. Albert, L. Fensterbank, E. Lacôte, and M. Malacria Top. Curr. Chem. 264 2006 1 62
16. P. Renaud, and M.P. Sibi Radicals in Organic Synthesis Vol. 1+2 2001 Wiley-VCH Weinheim
17. B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke, and F. Trach Org. React. 48 1996 301 856
18. Selected reviews: E. Brunoldi, M. Luparia, A. Porta, G. Zanoni, and G. Vidari Curr. Org. Chem. 10 2006 2259 2282
19. A. Padwa Pure Appl. Chem. 75 2003 47 62
20. Selected reviews: A. Padwa Helv. Chim. Acta 88 2005 1357 1374
21. G. Mehta, and S. Muthusamy Tetrahedron 58 2002 9477 9504
22. Reviews: D.J. Procter, R.A. Flowers II, and T. Skrydstrup Organic Synthesis Using Samarium Diiodide 2009 RSC Cambridge
23. D.J. Edmonds, D. Johnston, and D.J. Procter Chem. Rev. 104 2004 3371 3404
24. G.A. Molander, and C.R. Harris Tetrahedron 54 1998 3321 3354
25. Reviews: J.M. Cuerva, J. Justicia, J.L. Oller-Lopez, and J.E. Oltra Top. Curr. Chem. 264 2006 63 91
26. A.F. Barrero, J.F. Quílez del Moral, E.M. Sánchez, and J.F. Arteaga Eur. J. Org. Chem. 2006 1627 1641
27. Recent reviews: B.B. Snider Tetrahedron 65 2009 10738 10744
28. A.S. Demir, and M. Emrullahoglu Curr. Org. Synth. 4 2007 321 350
29. T. Linker J. Organomet. Chem. 661 2002 159 167
30. G.G. Melikyan Org. React. 49 1997 427 675
31. Reviews: V. Nair, and A. Deepthi Tetrahedron 65 2009 10745 10755
32. V. Nair, L. Balagopal, R. Rajan, and J. Mathew Acc. Chem. Res. 37 2004 21 30
33. V. Nair, S.B. Panicker, L.G. Nair, T.G. George, and A. Augustine Synlett 2003 156 165
34. V. Nair, J. Mathew, and J. Prabhakaran Chem. Soc. Rev. 26 1997 127 132
35. Reviews: K.D. Moeller Synlett 2009 1208 1218
36. K.D. Moeller Tetrahedron 56 2000 9527 9554
37. K.D. Moeller Top. Curr. Chem. 185 1997 49 86
38. U. Jahn, P. Hartmann, I. Dix, and P.G. Jones Eur. J. Org. Chem. 2001 3333 3355
39. U. Jahn, P. Hartmann, I. Dix, and P.G. Jones Eur. J. Org. Chem. 2002 718 735
40. U. Jahn, P. Hartmann, and E. Kaasalainen Org. Lett. 6 2004 257 260
41. U. Jahn, F. Kafka, R. Pohl, and P.G. Jones Tetrahedron 65 2009 10917 10929
42. U. Jahn, and E. Dinca Chem. - Eur. J. 15 2009 58 62
43. U. Jahn, and E. Dinca J. Org. Chem. 75 2010 4480 4491
44. U. Jahn, M. Müller, and S. Aussieker J. Am. Chem. Soc. 122 2000 5212 5213
45. U. Jahn Chem. Commun. 2001 1600 1601
46. For a recent review, see: C.F. Nising, and S. Bräse Chem. Soc. Rev. 37 2008 1218 1228
47. For other tandem addition/cyclization approaches to tetrahydrofurans, see: J.P. Wolfe, and M.B. Hay Tetrahedron 63 2007 261 290
48. Ref. 2b.
49. G. Balme, E. Bossharth, and N. Monteiro Eur. J. Org. Chem. 2003 4101 4111
50. G. Balme, D. Bouyssi, T. Lomberget, and N. Monteiro Synthesis 2003 2115 2134
51. K.C. Majumdar, P.K. Basu, and S.K. Chattopadhyay Tetrahedron 63 2007 793 826 and earlier reviews in this series
52. Preliminary communication: U. Jahn, and D. Rudakov Synlett 2004 1207 1210
53. For other studies, see: A.-C. Durand, E. Dumez, J. Rodriguez, and J.-P. Dulcre Chem. Commun. 1999 2437 2438
54. A.-C. Durand, J. Rodriguez, and J.-P. Dulcre Synlett 2000 731 733
55. A. Kamimura, A. Kadowaki, T. Yoshida, R. Takeuchi, and H. Uno Chem. - Eur. J. 15 2009 10330 10334
56. J.-P. Goddard, C. Gomez, F. Brebion, S. Beauvire, L. Fensterbank, and M. Malacria Chem. Commun. 2007 2929 2931
57. For an initial application, see: U. Jahn, and D. Rudakov Org. Lett. 8 2006 4481 4484
58. E. Dumez, A.-C. Durand, M. Guillaume, P.-Y. Roger, R. Faure, J.-M. Pons, G. Herbette, J.-P. Dulcre, D. Bonne, and J. Rodriguez Chem. - Eur. J. 15 2009 12470 12488
59. Review: S. Yamazaki Chem. - Eur. J. 14 2008 6026 6036: Some oxyl radicals add to alkynes: U. Wille, and C. Jargstorff J. Chem. Soc., Perkin Trans. 1 2002 1036 1041 and cited ref
60. B.B. Snider, and Q. Che Tetrahedron 58 2002 7821 7827
61. N. Arai, and K. Narasaka Bull. Chem. Soc. Jpn. 70 1997 2525 2534 and cited ref
62. W.R. Bowman, D.S. Brown, C.A. Burns, and D. Crosby J. Chem. Soc., Perkin Trans. 1 1994 2083 2090
63. W.R. Bowman, D.S. Brown, C.A. Burns, and D. Crosby J. Chem. Soc., Perkin Trans. 1 1993 2099 2105
64. D. Hobbs-Mallyon, and D.A. Whiting J. Chem. Soc., Chem. Commun. 1991 899 900
65. A.S. Kende, and K. Koch Tetrahedron Lett. 27 1986 6051 6054 For a recent β-nitro radical cyclization mediated by iron compounds see
66. T. Taniguchi, and H. Ishibashi Org. Lett. 12 2010 124 126
67. J.E. Wilson, A.D. Casarez, and D.W.C. MacMillan J. Am. Chem. Soc. 131 2009 11332 11334
68. For reviews on conjugate additions to nitroalkenes, see: O.M. Berner, L. Tedeschi, and D. Enders Eur. J. Org. Chem. 2002 1877 1894
69. M. Thirumalaikumar Org. Prep. Proced. Int. 43 2011 67 129
70. tBu
71. Q. Cheng, T. Oritani, T. Horiguchi, and Q. Shi Eur. J. Org. Chem. 1999 2689 2693
72. A. Hassner, O. Friedman, and W. Dehaen Liebigs Ann./Recl. 1997 587 594
73. A. Hassner, and W. Dehaen Chem. Ber. 124 1991 1181 1186 Using BuLi
74. H.R. Kim, K.M. Kim, J.N. Kim, and E.K. Ryu Synth. Commun. 24 1994 1107 1116
75. H.R. Kim, H.J. Kim, J.L. Duffy, M.M. Olmstead, K. Ruhlandt-Senge, and M.J. Kurth Tetrahedron Lett. 32 1991 4259 4262 Using KH or NaH
76. J.L. Duffy, J.A. Kurth, and M.J. Kurth Tetrahedron Lett. 34 1993 1259 1260
77. X. Beebe, C.L. Chiappari, M.J. Kurth, and N.E. Schore J. Org. Chem. 58 1993 7320 7321
78. KS.-L. Huang, E.H. Lee, M.M. Olmstead, and M.J. Kurth J. Org. Chem. 65 2000 499 503
79. Review: D. Seebach, A.K. Beck, and A. Studer Modern Synthetic Methods Vol. 7 1995 VCH Weinheim pp. 3-178; For a recent account on the reactivity of LiCl in conjugate additions, see
80. Y. Ma, A.C. Hoepker, L. Gupta, M.F. Faggin, and D.B. Collum J. Am. Chem. Soc. 132 2010 15610 15623
81. Isomerization of this nitrostyrene to the allylic isomer is apparently significantly faster than conjugate addition. For isomerizations, see: X. Sun, S. Sengupta, J.L. Petersen, H. Wang, J.P. Lewis, and X. Shi Org. Lett. 9 2007 4495 4498
82. R. Tamura, and L.S. Hegedus J. Am. Chem. Soc. 104 1982 3727 3729
83. R. Tamura, K. Hayashi, M. Kakihana, M. Tsuji, and D. Oda Tetrahedron Lett. 26 1985 851 854
84. R. Tamura, K. Hayashi, M. Kakihana, M. Tsuji, and D. Oda Chem. Lett. 1985 229 232
85. J.C. Ferrand, R. Schneider, P. Gérardin, and B. Loubinoux Synth. Commun. 26 1996 4329 4336
86. -.
87. Full crystallographic details for structure 13Da were deposited at the Cambridge Crystallographic Data Centre under the number CCDC-849156. This material may be obtained free of charge from http://www.ccdc.cam.ac.uk/products/ csd/request.
88. For the use of copper dicarboxylates in oxidative radical cyclizations, see: S.R. Chemler Org. Biomol. Chem. 7 2009 3009 3019 and cited ref
89. Y.-X. Jia, and E.P. Kündig Angew. Chem., Int. Ed. 48 2009 1636 1639
90. A. Perry, and R.J.K. Taylor Chem. Commun. 2009 3249 3251
91. D.S. Pugh, J.E.M.N. Klein, A. Perry, and R.J.K. Taylor Synlett 2010 934 938
92. J.E.M.N. Klein, A. Perry, D.S. Pugh, and R.J.K. Taylor Org. Lett. 12 2010 3446 3449 All these cyclizations require harsh conditions to proceed
93. For the application of iron β-diketonates in intramolecular radical coupling reactions, see: M.P. DeMartino, K. Chen, and P.S. Baran J. Am. Chem. Soc. 130 2008 11546 11560
94. J.M. Richter, Y. Ishihara, T. Masuda, B.W. Whitefield, T. Llamas, A. Pohjakallio, and P.S. Baran J. Am. Chem. Soc. 130 2008 17938 17954
95. Precedence for the formation of 16Aa from silyl nitronates: I.N.N. Namboothiri, and A. Hassner Top. Curr. Chem. 216 2001 1 49
96. For the influence of amines on the course of oxidative reactions, see: U. Jahn, and P. Hartmann J. Chem. Soc., Perkin Trans. 1 2001 2277 2282
97. Tetrahydrofurans 17-20 undergo stereospecific intramolecular alkylation reactions mediated by DBU, which provide 2-oxabicyclo[3.1.0]hexanes. From their relative configuration the configuration at the exocyclic centers in 17-20 as well as that of the nitro center of 17-20 can be established, see: Jahn, U.; Rudakov, D.; Jones, P. G. Tetrahedron 2012, 68, 447-463.
98. - during 1.5 h.
99. We thank a referee for this suggestion.
100. J.K. Kochi J.K. Kochi, Free Radicals Vol. 1 1973 Wiley New York, NY 591 683
101. B. Maillard, K.U. Ingold, and J.C. Scaiano J. Am. Chem. Soc. 105 1983 5095 5099
102. A.L.J. Beckwith, and C.H. Schiesser Tetrahedron 41 1985 3925 3941
103. D.C. Spellmeyer, and K.N. Houk J. Org. Chem. 52 1987 959 974
104. 1G: S.V. Kelkar, A.A. Arbale, G.S. Joshi, and G.H. Kulkarni Synth. Commun. 20 1990 839 847 2c, 2d
105. T.E. Stevens, and W.D. Emmons J. Am. Chem. Soc. 79 1957 6008 6014 2e
106. W.-W. Lin, Y.-J. Jang, Y. Wang, J.-T. Liu, S.-R. Hu, L.-Y. Wang, and C.-F. Yao J. Org. Chem. 66 2001 1984 1991
107. K.-H. Kao, C.-S. Yang, J.-T. Liu, W.-W. Lin, H.-Y. Fang, C.-F. Yao, and K. Chen Tetrahedron 54 1998 13997 14014
108. M.-C. Yan, J.-Y. Liu, W.-W. Lin, K.-H. Kao, J.-T. Liu, J.-J. Jang, and C.-F. Yao Tetrahedron 55 1999 12493 12514