Mn(III)-catalyzed radical reactions of 1,3-dicarbonyl compounds and cyclopropanols with vinyl azides for divergent synthesis of azaheterocycles

Chimia

Volumn 66, Issue 6, 2012, Pages 377-381

  Chiba, Shunsuke ^a  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

1,3 Dicarbonyl compounds; Azaheterocycles; Cyclopropanols; Manganese; Radicals; Vinyl azides

Indexed keywords

EID: 84863742633     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2012.377     Document Type: Article

References (46)

1. For recent reviews, see: a) G. L. Thomas, C. W. Johannes, Curr. Opin. Chem. Biol. 2011, 15, 516;
2. R. Tohme, N. Darwiche, H. Gali-Muhtasib, Molecules 2011, 16, 9665;
3. S. Dandapani, L. A. Marcaurelle, Curr. Opin. Chem. Biol. 2010, 14, 362;
4. M. E. Welsch, S. A. Snyder, B. R. Stockwell, Curr. Opin. Chem. Biol. 2010, 14, 347;
5. J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337.
6. J. A. Joule, K. Mills, 'Heterocyclic Chemistry', 5th edition, Wiley-Blackwell, 2010;
7. 'Progress in Heterocyclic Chemistry', Eds. G. W. Gribble, J. A. Joule, Elsevier: Oxford, 2008; Vol. 20 and others in this series;
8. 'Comprehensive Heterocyclic Chemistry III', Eds. A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Pergamon: Oxford, 2008;
9. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles; Wiley-VCH: Weinheim, 2003.
10. B. M. Trost, Angew. Chem. Int. Ed. 1995, 34, 259;
11. B. M. Trost, Science 1991, 254, 1471.
12. P. A. Wender, V. A. Verma, T. J. Paxton, T. H. Pillow, Acc. Chem. Res. 2008, 41, 40.
13. P. A. Wender, M. P. Croatt, B. Witulski, Tetrahedron 2006, 62, 7505.
14. For a prior account on our azide chemistry, see S. Chiba, Synlett 2012, 23, 21.
15. For a review, see: K. Banert, in 'Organic Azides: Syntheses and Applications', Eds. S. Bräse, K. Banert, Wiley, 2010; p. 115.
16. For our recent works on heterocycle synthesis using 2H-azirines generated from vinyl azides, see: a) E. P. J. Ng, Y.-F. Wang, B. W.-Q. Hui, G. Lapointe, S. Chiba, Tetrahedron 2011, 67, 7728.
17. S. Chiba, Y.-F. Wang, G. Lapointe, K. Narasaka, Org. Lett. 2008, 10, 313.
18. C. J. Moody, in 'Comprehensive Organic Synthesis', Eds. B. M. Trost, I. Fleming, S. Ley, Pergamon: Oxford, 1991; Vol. 7, p 21;
19. G. Smolinsky, C. A. Pryde, J. Org. Chem. 1968, 33, 2411;
20. G. L'abbe, Angew. Chem., Int. Ed. Engl. 1975, 14, 775;
21. H. Hemetsberger, D. Knittle, H. Weidmann, Monatsh. Chem. 1970, 101, 161;
22. A. R. MacKenzie, C. J. Moody, C. W. Rees, J. Chem. Soc., Chem. Commun. 1983, 1372;
23. R. E. Bolton, C. J. Moody, M. Pass, C. W. Rees, G. Tojo, J. Chem. Soc., Perkin Trans. 1 1988, 2491.
24. Fe (ii) - and Rh (ii)-catalyzed indole formation from azidocinnamates was reported, see: a) J. Bonnamour, C. Bolm, Org. Lett. 2011, 13, 2012;
25. B. J. Stokes, H. Dong, B. E. Lesile, A. L. Pumphrey, T. G. Driver, J. Am. Chem. Soc. 2007, 129, 7500.
26. A. Suzuki, Tetrahedron Lett. 1975, 2195.
27. B. P. Roberts, Tetrahedron Lett. 1983, 24, 3779.
28. J. B. Bush, Jr., H. Finkbeiner, J. Am. Chem. Soc. 1968, 90, 5903;
29. E. I. Heiba, R. M. Sessau, W. J. Koehl, Jr. J. Am. Chem. Soc. 1968, 90, 5905.
30. For selected reviews, see: a) B. B. Snider, Chem. Rev. 1996, 96, 339;
31. B. B. Snider, in 'Radicals in Organic Synthesis', Vol. 1, Eds. P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, 2001, p. 198.
32. N. Iwasawa, S. Hayakawa, M. Funahashi, K. Isobe, K. Narasaka, Bull. Chem. Soc. Jpn. 1993, 66, 819;
33. N. Iwasawa, S. Hayakawa, K. Isobe, K. Narasaka, Chem. Lett. 1991, 1193.
34. E. P. J. Ng, Y.-F. Wang, S. Chiba, Synlett 2011, 783;
35. Y.-F. Wang, K. K. Toh, S. Chiba, K. Narasaka, Org. Lett. 2008, 10, 5019.
36. S. A. Richert, P. K. S. Tsang, D. T. Sawyer, Inorg. Chem. 1988, 27, 1814.
37. Y.-F. Wang, K. K. Toh, E. P. J. Ng, S. Chiba, J. Am. Chem. Soc. 2011, 133, 6411;
38. Y.-F. Wang, S. Chiba, J. Am. Chem. Soc. 2009, 133, 12570.
39. H. Du, J. Long, Y. Shi, Org. Lett. 2006, 8, 2827.
40. For discussion on racemization of cyclohexyl radicals, see: a) A. J. Buckmelter, A. I. Kim, S. D. Rychnovsky, J. Am. Chem. Soc. 2000, 122, 9386;
41. B. P. Roberts, A. J. Steel, J. Chem. Soc., Perkin Trans. II 1992, 2025, and references therein.
42. For a review on synthesis of 2-azabicyclo[3.3.1] nonanes, see: J. Bonjoch, F. Diaba, B. Bradshaw, Synthesis 2011, 993.
43. E. Bächli, C. Vamvacas, H. Schmid, P. Karrer, Helv. Chim. Acta 1957, 40, 1167.
44. R. P. Borris, A. Guggisberg, M. Hesse, Helv. Chim. Acta 1984, 67, 455.
45. J. Quirante, C. Escolano, A. Merino, J. Bonjoch, J. Org. Chem. 1998, 63, 968;
46. J. Quirante, C. Escolano, J. Bosch, J. Bonjoch, J. Chem. Soc., Chem. Commun. 1995, 2141.