Radical cyclization cascades of unsaturated Meldrum's acid derivatives

Organic Letters

Volumn 14, Issue 1, 2012, Pages 146-149

  Sautier, Brice ^a   Lyons, Sarah E ^a   Webb, Michael R ^b   Procter, David J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIOXANE DERIVATIVE; MELDRUM ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

CYCLIZATION; DIOXANES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84855497484     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2029367     Document Type: Article

References (41)

1. Finley, K. T. Chem. Rev. 1964, 64, 573
2. Rühlmann, K. Synthesis 1971, 236
3. Bloomfield, J. J.; Owsley, D. C.; Ainsworth, C.; Robertson, R. E. J. Org. Chem. 1975, 40, 393
4. Kashimura, S.; Murai, Y.; Ishifune, M.; Masuda, H.; Murase, H.; Shono, T. Tetrahedron Lett. 1995, 36, 4805
5. Makosza, M.; Grela, K. Synlett 1997, 267
6. Bouveault, L.; Blanc, G. Compt. Rend. 1903, 136, 1676
7. Bouveault, L.; Blanc, G. Bull. Soc. Chim. Fr. 1904, 31, 666
8. Chablay, E. Compt. Rend. 1913, 156, 1020
9. Bodnar, B. S.; Vogt, P. F. J. Org. Chem. 2009, 74, 2598
10. Duffy, L. A.; Matsubara, H.; Procter, D. J. J. Am. Chem. Soc. 2008, 130, 1136
11. Guazzelli, G.; De Grazia, S.; Collins, K. D.; Matsubara, H.; Spain, M.; Procter, D. J. J. Am. Chem. Soc. 2009, 131, 7214
12. Parmar, D.; Duffy, L. A.; Sadasivam, D. V.; Matsubara, H.; Bradley, P. A.; Flowers, R. A., II; Procter, D. J. J. Am. Chem. Soc. 2009, 131, 15467
13. Collins, K. D.; Oliveira, J. M.; Guazzelli, G.; Sautier, B.; De Grazia, S.; Matsubara, H.; Helliwell, M.; Procter, D. J. Chem.-Eur. J. 2010, 16, 10240
14. Parmar, D.; Price, K.; Spain, M.; Matsubara, H.; Bradley, P. A.; Procter, D. J. J. Am. Chem. Soc. 2011, 133, 2418
15. 3) but proposed that radical-anions at a lower oxidation state were involved: Cossy, J.; Gille, B.; Bellosta, V. J. Org. Chem. 1998, 63, 3141
16. 3): Srikrishna, A.; Ramasastry, S. S. V. Tetrahedron Lett. 2004, 45, 379
17. Szostak, M.; Spain, M.; Parmar, D.; Procter, D. J. Chem. Commun. 2011, DOI: 10.1039/C1CC14252F.
18. Szostak, M.; Procter, D. J. Angew. Chem., Int. Ed. 2011, 50, 7737
19. Procter, D. J.; Flowers, R. A., II; Skrydstrup, T. Organic Synthesis using Samarium Diiodide: A Practical Guide; RSC Publishing: Cambridge, 2010.
20. Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009, 48, 7140
21. Gopalaiah, K.; Kagan, H. B. New J. Chem. 2008, 32, 607
22. Kagan, H. B. Tetrahedron 2004, 59, 10351
23. Dahlén, A.; Hilmersson, G. Eur. J. Inorg. Chem. 2004, 3393
24. Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371
25. Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727
26. Kagan, H. B.; Namy, J. L. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: Berlin, 1999; p 155.
27. Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321
28. Hutton, T. K.; Muir, K. W.; Procter, D. J. Org. Lett. 2003, 5, 4811
29. Chopade, P. R.; Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2004, 126, 44
30. Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2005, 127, 18093
31. Sadasivam, D. V.; Teprovich, J. A., Jr.; Procter, D. J.; Flowers, R. A., II. Org. Lett. 2010, 12, 4140
32. Yacovan, A.; Hoz, S.; Bilkis, I. J. Am. Chem. Soc. 1996, 118, 261
33. Tarnopolsky, A.; Hoz, S. Org. Biomol. Chem. 2007, 5, 3801
34. Tarnopolsky, A.; Hoz, S. J. Am. Chem. Soc. 2007, 129, 3402
35. Amiel-Levy, M.; Hoz, S. J. Am. Chem. Soc. 2009, 131, 8280
36. Upadhyay, S. K.; Hoz, S. J. Org. Chem. 2011, 76, 1355
37. Szostak, M.; Spain, M.; Procter, D. J. Chem. Commun. 2011, 47, 10254
38. For a review of the chemistry of Meldrum's acid, see: McNab, H. Chem. Soc. Rev. 1978, 7, 345
39. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168
40. Samojłowicz, C.; Bieniek, M.; Grela, K. Chem. Rev. 2009, 109, 3708
41. Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746