4-(1-Haloalkyl)-3-nitrotetrahydrofurans as versatile scaffolds for the synthesis of diversely functionalized tetrahydrofurans

Tetrahedron

Volumn 68, Issue 2, 2012, Pages 447-463

  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

3 oxabicyclo 3.1.0 hexanes; Aminotetrahydrofurans; Hydrogenation; Oxidation

Indexed keywords

4 (1 HALOALKYL) 3 NITROTETRAHYDROFURAN; AMINE; NITROFURAN DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CONTROLLED STUDY; CYCLOPROPANATION; EPIMERIZATION; OXIDATION; PRIORITY JOURNAL; REACTION TIME; REDUCTION; SUBSTITUTION REACTION; TEMPERATURE;

EID: 82955203417     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.11.023     Document Type: Article

References (46)

1. L.F. Tietze, G. Brasche, and K. Gericke Domino Reactions in Organic Synthesis 2006 Wiley-VCH Weinheim
2. U. Jahn, D. Rudakov, and P.G. Jones Tetrahedron 68 2012 accepted for publication
3. U. Jahn, and D. Rudakov Synlett 2004 1207 1210
4. Initial results: U. Jahn, and D. Rudakov Org. Lett. 8 2006 4481 4484
5. Recent review: R.R. Schmidt, and Y.D. Vankar Acc. Chem. Res. 41 2008 1059 1073
6. Review: H. Rosemeyer Chem. Biodiversity 1 2004 361 401
7. H. Vorbrüggen, and C. Ruh-Pohlenz Handbook of Nucleoside Synthesis 2001 Wiley New York, NY
8. H. Vorbrüggen, and C. Ruh-Pohlenz L.A. Paquette, Organic Reactions Vol. 55 2000 John Wiley New York, NY 1 630
9. Reviews: F.G. Njoroge, K.X. Chen, N.-Y. Shih, and J.J. Piwinski Acc. Chem. Res. 41 2008 50 59
10. N. Araújo, M.V. Gil, E. Román, and J.A. Serrano Tetrahedron: Asymmetry 20 2009 1999 2006 and cited ref
11. R.N. Bwire, R.R. Majinda, I.B. Masesane, and P.G. Steel Pure Appl. Chem. 81 2009 105 112 and cited ref
12. I.B. Masesane, A.S. Batsanov, J.A.K. Howard, R. Mondal, and P.G. Steel Beilstein J. Org. Chem. 2 2006
13. S.Y. Mahmood, M.-C. Lallemand, L. Sader-Bakaouni, O. Charton, P. Vérité, H. Dufat, and F. Tillequin Tetrahedron 60 2004 5105 5110 and cited ref
14. O. Klenz, R. Evers, R. Miethchen, and M. Michalik J. Fluorine Chem. 81 1997 205 210
15. N. Hossain, J. Plavec, C. Thibaudeau, and J. Chattopadhyaya Tetrahedron 49 1993 9079 9088 and cited ref
16. P.A. Grieco, R. Lis, R.E. Zelle, and J. Finn J. Am. Chem. Soc. 108 1986 5908 5919 and cited ref
17. G. Just, T.J. Liak, M.-I. Lim, P. Potvin, and Y.S. Tsantrizos Can. J. Chem. 58 1980 2024 2033 By [3+2] cycloadditions
18. V. Nair, S. Mathai, and R.L. Varma J. Org. Chem. 69 2004 1413 1414
19. A. Hassner, O. Friedman, and W. Dehaen Liebigs Ann./Recl. 1997 587 594
20. C. Cativiela, and M. Ordóñez Tetrahedron: Asymmetry 20 2009 1 63
21. S. Hanessian, and L. Auzzas Acc. Chem. Res. 41 2008 1241 1251
22. F. Brackmann, and A. de Meijere Chem. Rev. 107 2007 4538 4583
23. G.R. Krow, and K.C. Cannon Org. Prep. Proced. Int. 32 2000 103 122
24. S.A.W. Gruner, E. Locardi, E. Lohof, and H. Kessler Chem. Rev. 102 2002 491 514
25. M.D.P. Risseeuw, M. Overhand, G.W.J. Fleet, and M.I. Simone Tetrahedron: Asymmetry 18 2007 2001 2010
26. S.H. Gellman Acc. Chem. Res. 31 1998 173 180
27. D.J. Hill, M.J. Mio, R.B. Prince, T.S. Hughes, and J.S. Moore Chem. Rev. 101 2001 3893 4011
28. G. Licini, L.J. Prins, and P. Scrimin Eur. J. Org. Chem. 2005 969 977
29. S. Hecht, and I. Huc Foldamers. Structure, Properties and Applications 2007 Wiley-VCH Weinheim
30. W.S. Horne, and S.H. Gellman Acc. Chem. Res. 41 2008 1399 1408
31. E.B. Averina, N.V. Yashin, T.S. Kuznetsova, and N.S. Zefirov Russ. Chem. Rev. 78 2009 887 902
32. R. Ballini, A. Palmieri, and D. Fiorini ARKIVOC 2007 172 194 Pt. 7. For an oxidative direct approach, see
33. A. Kamimura, A. Kadowaki, T. Yoshida, R. Takeuchi, and H. Uno Chem. - Eur. J. 15 2009 10330 10334
34. Full crystallographic details were deposited at the Cambridge Crystallographic Data Centre under the numbers CCDC-848779 (6a), CCDC-848780 (8), CCDC-848781 (22j), CCDC-848782 (27f). This material may be obtained free of charge from http://www.ccdc.cam.ac.uk/products/csd/request.
35. Review: L.N. Mander, and C.M. Williams Tetrahedron 59 2003 1105 1136
36. Recent review: R. Ballini, and M. Petrini Tetrahedron 60 2004 1017 1047
37. Overview: T.J. Caggiano S.D. Burke, R.L. Danheiser, Handbook of Reagents for Organic Synthesis. Oxidizing and Reducing Agents 1999 Wiley Chichester, UK 246 250
38. H.-U. Blaser, H. Steiner, and M. Studer ChemCatChem 1 2009 210 221
39. R. Ballini, and M. Petrini ARKIVOC 2009 195 223 Pt. 9
40. A.O. King, R.D. Larsen, and E.-I. Negishi E.-I. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 2002 Wiley Hoboken 2719 2752
41. F. Figueras, and B. Coq J. Mol. Catal. A: Chem. 173 2001 223 230
42. J. Tormo, D.S. Hays, and G.C. Fu J. Org. Chem. 63 1998 5296 5297
43. A. Voituriez, J. Moulinas, C. Kouklovsky, and Y. Langlois Synthesis 2003 1419 1426
44. M.J. Crossley, Y.M. Fung, E. Kyriakopoulos, and J.J. Potter J. Chem. Soc., Perkin Trans. 1 1998 1123 1130
45. Z.J. Witczak, R. Chhabra, and J. Chojnacki Tetrahedron Lett. 38 1997 2215 2218
46. A. Barco, S. Benetti, C. De Risi, G.P. Pollini, R. Romagnoli, and V. Zanirato Tetrahedron Lett. 37 1996 7599 7602