Selective reductions of cyclic 1,3-diesters by using SmI2 and H2O

Chemistry - A European Journal

Volumn 16, Issue 33, 2010, Pages 10240-10249

  Collins, Karl D ^a   Oliveira, Juliana M ^a   Guazzelli, Giuditta ^a   Sautier, Brice ^a   De Grazia, Sara ^a   Matsubara, Hiroshi ^b   Helliwell, Madeleine ^a   Procter, David J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b Osaka Prefecture University   (Japan)

Author keywords

Chemoselectivity; Cyclization; Radical reactions; Reduction; Samarium

Indexed keywords

CHEMO-SELECTIVITY; CYCLIZATIONS; DIASTEREO-SELECTIVITY; DIESTERS; ESTER CARBONYL GROUP; HYDROXYACIDS; INTRAMOLECULAR ADDITIONS; ONE-ELECTRON REDUCTIONS; RADICAL REACTIONS; REACTION TEMPERATURE; REAGENT SYSTEMS; SELECTIVE REDUCTION; STEREOCENTERS; STEREOCONTROL;

ESTERIFICATION; ESTERS; OLEFINS; REACTION KINETICS; SAMARIUM;

CYCLIZATION;

DIOXANE DERIVATIVE; ESTER; FREE RADICAL; HYDROXYACID; IODIDE; REDUCING AGENT; SAMARIUM; SAMARIUM DIIODIDE; WATER;

ARTICLE; CHEMISTRY; SYNTHESIS;

DIOXANES; ESTERS; FREE RADICALS; HYDROXY ACIDS; IODIDES; REDUCING AGENTS; SAMARIUM; WATER;

EID: 77956128342     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000632     Document Type: Article

References (46)

1. 2 in synthesis:
2. T. Skrydstrup, Angew. Chem. 1997, 109, 355;
3. Angew. Chem. Int. Ed. Engl. 1997, 36, 345;
4. G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321;
5. H. B. Kagan, J. L. Namy in Lanthanides: Chemistry and Use in Organic Synthesis (Ed.: S. Kobayashi), Springer, Berlin, 1999, p. 155;
6. P. G. Steel, J. Chem. Soc. Perkin Trans. 1 2001, 2727;
7. H. B. Kagan, Tetrahedron 2003, 59, 10351;
8. A. Dahlén, G. Hilmersson, Eur. J. Inorg. Chem. 2004, 3393;
9. D. J. Edmonds, D. Johnston, D. J. Procter, Chem. Rev. 2004, 104, 3371;
10. K. Gopalaiah, H. B. Kagan, New J. Chem. 2008, 32, 607;
11. K. C. Nicolaou, S. P. Ellery, J. S. Chen, Angew. Chem. 2009, 121, 7276;
12. Angew. Chem. Int. Ed. 2009, 48, 7140;
13. D. J. Procter, R. A. Flowers II, T. Skrydstrup, Organic Synthesis using Samarium Diiodide: A Practical Guide; RSC, Cambridge, 2010.
14. a) L. A. Duffy, H. Matsubara, D. J. Procter, J. Am. Chem. Soc. 2008, 130, 1136;
15. D. Parmar, L. A. Duffy, D. V. Sadasivam, H. Matsubara, P. A. Bradley, R. A. Flowers II, D. J. Procter, J. Am. Chem. Soc. 2009, 131, 15467.
16. G. Guazzelli, S. De Grazia, K. D. Collins, H. Matsubara, M. Spain, D. J. Procter, J. Am. Chem. Soc. 2009, 131, 7214.
17. a) B. Chen, Heterocycles 1991, 32, 529;
18. H. McNab, Chem. Soc. Rev. 1978, 7, 345.
19. M. O. Polla, L. Tottie, C. Norden, M. Linschoten, D. Müsil, S. Trumpp-Kallmeyer, I. R. Aukrust, R. Ringom, K. H. Holm, S. M. Neset, M. Sandberg, J. Thurmond, P. Yu, G. Hategan, H. Anderson, Bioorg. Med. Chem. 2004, 12, 1151.
20. 2:
21. A. Dahlén, G. Hilmersson, B. W. Knettle, R. A. Flowers II, J. Org. Chem. 2003, 68, 4870;
22. A. Tarnopolsky, S. Hoz, Org. Biomol. Chem. 2007, 5, 3801.
23. a) P. R. Chopade, E. Prasad, R. A. Flowers II, J. Am. Chem. Soc. 2004, 126, 44;
24. E. Prasad, R. A. Flowers II, J. Am. Chem. Soc. 2005, 127, 18093;
25. R. J. Enemaerke, K. Daasbjerg, T. Skrydstrup, Chem. Commun. 1999, 343;
26. M. Shabangi, R. A. Flowers II, Tetrahedron Lett. 1997, 38, 1137.
27. Axial radicals are preferred due to an anomeric effect. For selected examples, see: a) V. Malatesta, K. U. Ingold, J. Am. Chem. Soc. 1981, 103, 609;
28. B. Giese, J. Dupuis, Tetrahedron Lett. 1984, 25, 1349;
29. T. Cohen, M. Bhupathy, Acc. Chem. Res. 1989, 22, 152;
30. D. Crich, L. B. L. Lim, J. Chem. Soc. Perkin Trans. 1 1991, 2209. See also reference [13b].
31. Calculated relative reaction energies suggest that the degree of substitution on the cyclic 1, 3-diesters does not affect the ease of reduction significantly. See reference [3].
32. H. Farran, S. Hoz, Org. Lett. 2008, 10, 4875.
33. a) J. Cossy has described the radical cyclization of unsaturated esters by using sodium-ammonia but proposes that radicals at a lower oxidation state are involved: J. Cossy, B. Gille, V. Bellosta, J. Org. Chem. 1998, 63, 3141;
34. Srikrishna has reported the anionic cyclization of unsaturated esters by using lithium-ammonia: A. Srikrishna, S. S. V. Ramasastry, Tetrahedron Lett. 2004, 45, 379;
35. 2, see: R. H. Taaning, L. Thim, J. Karaffa, A. G. Campaña, A.-M. Hansen, T. Skrydstrup, Tetrahedron 2008, 64, 11884.
36. See the Supporting Information for X-ray crystal structures and CCDC numbers.
37. For recent discussions of radical versus anionic cyclizations, see: a) W. F. Bailey, M. J. Mealy, K. B. Wiberg, Org. Lett. 2002, 4, 791, and references therein;
38. S. D. Rychnovsky, T. Hata, A. I. Kim, A. J. Buckmelter, Org. Lett. 2001, 3, 807. See also reference [11b].
39. A. Dahlén, G. Hilmersson, Tetrahedron Lett. 2001, 42, 5565, and references [6a] and [7b].
40. A. L. J. Beckwith, Tetrahedron 1981, 37, 3073.
41. Radical cyclizations tend to form cis-fused bicyclic products. For discussions, see: a) D. L. J. Clive, D. R. Cheshire, L. Set, J. Chem. Soc. Chem. Commun. 1987, 353;
42. D. L. J. Clive, H. W. Manning, T. L. B. Boivin, M. H. D. Postema, J. Org. Chem. 1993, 58, 6857.
43. For selected examples of reversible metal-mediated radical cyclizations, see: a) D. P. Curran, T. M. Morgan, C. E. Schwartz, B. B. Snider, M. A. Dombroski, J. Am. Chem. Soc. 1991, 113, 6607;
44. K. Sung, Y. Y. Wang, J. Org. Chem. 2003, 68, 2771.
45. 2-mediated transannular cyclizations involving conventional radical anions derived from ketones, see: G. A. Molander, B. Czako, M. Rheam, J. Org. Chem. 2007, 72, 1755.
46. No other diastereoisomers were isolated from the cyclizations of substrates 51-53.