Iron-mediated one-pot formal nitrocyclization onto unactivated alkenes

Organic and Biomolecular Chemistry

Volumn 9, Issue 3, 2011, Pages 653-655

  Taniguchi, Tsuyoshi ^a   Fujii, Tatsuya ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EFFICIENT METHOD; EXPERIMENTAL PROCEDURE; HETEROCYCLES; INTRAMOLECULAR MICHAEL ADDITION; IRON NITRATES; LOW TOXICITY; ONE POT; ONE-POT SYNTHESIS;

ADDITION REACTIONS; IRON COMPOUNDS; OLEFINS;

SYNTHESIS (CHEMICAL);

ALKENE; HETEROCYCLIC COMPOUND; IRON; NITRO DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION;

ALKENES; CYCLIZATION; HETEROCYCLIC COMPOUNDS; IRON; MOLECULAR STRUCTURE; NITRO COMPOUNDS;

EID: 79251478447     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00905a     Document Type: Article

References (41)

1. H. Feuer and T. Nielsen, Nitro compounds: Recent Advances in Synthesis and Chemistry, VCH, New York, 1990
2. N. Ono, The Nitro Group in Organic Synthesis, John Wiley-VCH, New York, 2001
3. A. G. M. Barrett G. G Graboski Chem. Rev. 1986 86 751
4. R. Ballini, E. Marcantoni and M. Petrini, In Amino Group Chemistry, A. Ricci, Ed., Wiley-VCH, 2008, pp 93-148
5. R. Ballini M. Petrini ARKIVOC 2009 195
6. For reviews on nitration reactions, see: G. A. Olah, R. Malhotra and S. C. Narang, Nitration: Methods and Mechanisms, VCH Publishers Inc., New York, 1989
7. T. Mori H. Suzuki Synlett 1995 383
8. T. Suzuki R. Noyori Chemtracts 1997 10 813
9. A. V. Stepanov V. V. Veselovsky Russ. Chem. Rev. 2003 72 327
10. Recent examples of nitration reactions, see: L. Grossi P. C. Montevecchi S. Strazzari Eur. J. Org. Chem. 2001 741
11. Y. Nishiwaki S. Sakaguchi Y. Ishii J. Org. Chem. 2002 67 5663
12. L. Grossi P. C. Montevecchi Chem.-Eur. J. 2002 8 380
13. K. Jayakanthan K. P. Madhusudanan Y. D. Vankar Tetrahedron 2004 60 397
14. B. P. Fors S. L. Buchwald J. Am. Chem. Soc. 2009 131 12898 See also ref. 7
15. T. Taniguchi H. Ishibashi Org. Lett. 2010 12 124
16. T. Taniguchi T. Fujii H. Ishibashi J. Org. Chem. 2010 10.1021/jo101769d
17. Examples of synthesis of nitroalkenes, see: F. G. Bordwell E. W. Garbisch, Jr. J. Org. Chem. 1962 27 2322
18. E. J. Corey H. Estreicher J. Am. Chem. Soc. 1978 100 6294
19. W. W. Sy A. W. By Tetrahedron Lett. 1985 26 1193
20. E. Hata T. Yanada T. Mukaiyama Bull. Chem. Soc. Jpn. 1995 68 3629
21. P. J. Campos B. García M. A. Rodríguez Tetrahedron Lett. 2000 41 979
22. I. Jovel S. Prateeptongkum R. Jackstell N. Vogl C. Weckbecker M. Beller Adv. Synth. Catal. 2008 350 2493
23. Reviews, see: M. D. Dowle D. I. Davies Chem. Soc. Rev. 1979 8 171
24. G. Cardillo M. Orena Tetrahedron 1990 46 3321
25. J. Mulzer, In Organic Synthesis Highlights, J. Mulzer, H. J. Altenbach, M. Braun, K. Krohn, and, H. U. Reissig, ed., VCH, Weinheim, 1991, pp 158-164
26. G. Rousseau S. Robin Tetrahedron 1998 54 13681
27. S. Robin G Rousseau Eur. J. Org. Chem. 2002 3099
28. K. H. Jensen M. S. Sigman Org. Biomol. Chem. 2008 6 4083
29. S. Minakata Acc. Chem. Res. 2009 42 1172
30. Recent examples, see: M. C. Marcotullio V. Campagna S. Sternativo F. Costantino M. Curini Synthesis 2006 2760
31. S. Minakata Y. Morino Y. Oderaotoshi M Kamatsu Org. Lett. 2006 8 3335
32. T. J. Donohoe P. C. M. Winship D. S. Walter J. Org. Chem. 2009 74 6394
33. T. Wu G. Yin G. Liu J. Am. Chem. Soc. 2009 131 16354
34. P. A. Sibbald F. E. Michael Org. Lett. 2009 11 1147
35. A. K. Verma T. Aggarwal V. Rustagi R. C. Larock Chem. Commun. 2010 46 4064
36. S. Mehta R. C. Larock J. Org. Chem. 2010 75 1652
37. 2Cl has been reported, see: H. Shechter F. Conrad A. L. Daulton R. B. Kaplan J. Am. Chem. Soc. 1952 74 3052
38. It has been reported that 5-exo-trig intramolecular Michael addition of a 2-substituted toluenesulfonamide derivative gave a cis-pyrrolidine compound in good diastereomeric selectivity, see: R. E. Dolle C.-S. Li A. N. Shaw Tetrahedron Lett. 1989 30 4723
39. 1H NMR signals of 5-H of these compounds are 4.71 (1H, app. t, J = 6.6 Hz, for 2f), 4.79 (1H, dd, app. t, J = 7.0 Hz, for cis-4) and 5.06 (1H, d, J = 8.5 Hz, for trans-4), see: P. Evans T. McCabe B. S. Morgan S. Reau Org. Lett. 2005 7 43
40. Synthesis of a β-lactam derivative by intramolecular Michael addition of unsaturated amides has been reported, see: Y.-H. W. J. R. Corrigan R. F. Feldkamp J. Org. Chem. 1961 26 1531
41. For a recent study of selectivity in O-cyclizations or N-cyclizations of unsaturated amides using electrophiles, see: T. Hu K. Liu M. Shen X. Yuan Y. Tang C. Li J. Org. Chem. 2007 72 8555 and references therein