Radical-mediated hydroxyalkylation of α,β-unsaturated esters

Tetrahedron

Volumn 61, Issue 43, 2005, Pages 10203-10215

  Yajima, Tomoko ^a   Saito, Chiaki ^a   Nagano, Hajime ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

, Unsaturated esters; Hydroxy esters; Hydroxyalkylation; Radical reaction; Tanikolide

Indexed keywords

BORANE DERIVATIVE; ESTER DERIVATIVE; IODINE DERIVATIVE; POLYKETIDE; POTASSIUM IODIDE; RADICAL; TANIKOLIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; ALKYLATION; ARTICLE; COLUMN CHROMATOGRAPHY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 25144484437     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.039     Document Type: Article

References (60)

1. For books, see: (a) J. Fossey, D. Lefort, and J. Sorba Free Radicals in Organic Chemistry 1995 Wiley Masson
2. P. Renaud, and M.P. Sibi Radicals in Organic Synthesis Vols. 1-2 2001 VCH Weinheim
3. S.Z. Zard Radical Reactions in Organic Synthesis 2003 Oxford University Press Oxford
4. For books, see: (a) G.M. Coppola, and H.F. Schuster Hydroxy acids in Enantioselective Synthesis 1997 VCH Weinheim
5. S. Hanessian Total Synthesis of Natural Products. The Chiron Approach 1983 Pergamon New York Chapter 2
6. T. Punniyamurthy, B. Bhatia, and J. Iqbal J. Org. Chem. 59 1994 850 853
7. T. Iwahama, S. Sakaguchi, and Y. Ishii J. Chem. Soc. 2000 613 614
8. K. Hirano, T. Iwahama, S. Sakaguchi, and Y. Ishii J. Chem. Soc. 2000 2457 2458
9. T. Hara, T. Iwahama, S. Sakaguchi, and Y. Ishii J. Org. Chem. 66 2001 6425 6431
10. H. Nagano, S. Toi, and T. Yajima Synlett 1999 53 54
11. H. Nagano, T. Hirasawa, and T. Yajima Synlett 2000 1073 1075
12. H. Nagano, M. Matsuda, and T. Yajima J. Chem. Soc., Perkin Trans. 1 2001 174 182
13. H. Nagano, S. Toi, T. Hirasawa, M. Matsuda, S. Hirasawa, and T. Yajima J. Chem. Soc., Perkin Trans. 1 2002 2525 2538
14. H. Nagano, H. Ohkouchi, and T. Yajima Tetrahedron 59 2003 3649 3663
15. The hydroxytrifluoromethylation of α,β-unsaturated esters via carbocation intermediates by electrooxidation, see: K. Uneyama, S. Watanabe, Y. Tokunaga, K. Kitagawa, and Y. Sato Bull. Chem. Soc. Jpn. 54 1992 1976 1981
16. A part of the results in this article has been reported as a preliminary letter: T. Yajima, H. Nagano, and C. Saito Tetrahedron Lett. 44 2003 7027 7029
17. J.E. Leibner, and J. Jacobus J. Org. Chem. 44 1979 449 550
18. O-Alkylation of PhOH with alkyl halide in the presence of KF, see: (a) J.H. Clark, and J.M. Miller J. Chem. Soc., Chem. Commun. 1976 229 230
19. J.H. Clark, H.L. Holland, and J.M. Miller Tetrahedron Lett. 38 1976 3361 3364
20. J.H. Clark, and J.M. Miller J. Am. Chem. Soc. 99 1977 498 504
21. Transformations of halides to the corresponding alcohols using aqueous carbonate has been reported: (a) J.G. Smith, P.W. Dibble, and R.E. Sandborn J. Org. Chem. 51 1986 3762 3768
22. J. Ji, C. Zhang, and X. Lu J. Org. Chem. 60 1995 1160 1169
23. B. Giese Angew. Chem., Int. Ed. Engl. 22 1983 753 764
24. +- OH×2] 258.0868, found 258.0852
25. 13C NMR spectra with those of 30.
26. S. Kobayashi, and I. Hachiya J. Org. Chem. 59 1994 3590 3596
27. H. Nagano, and Y. Kuno J. Chem. Soc., Chem. Commun. 1994 987 988
28. H. Nagano, Y. Kuno, Y. Omori, and M. Iguchi J. Chem. Soc., Perkin Trans. 1 1996 389 394
29. M.P. Sibi, J. Ji, J.B. Sausker, and C.P. Jasperse J. Am. Chem. Soc. 121 1999 7517 7526
30. N. Inamoto, and S. Masuda Chem. Lett. 1982 1003 1006
31. R.J. Boyd, and S.L. Boyd J. Am. Chem. Soc. 114 1992 1652 1655
32. C.H. Suresh, and N. Koga J. Am. Chem. Soc. 124 2002 1790 1797
33. M.S. Kharasch, E.V. Jensen, and W.H. Urry Science 102 1945 128
34. M.S. Kharasch, P.S. Skell, and P. Fisher J. Am. Chem. Soc. 70 1948 1055 1059
35. C.H. Schiesser, and L.M. Wild Tetrahedron 52 1996 13265 13314
36. D.P. Curran, E. Bosch, J. Kaplan, and M. Newcomb J. Org. Chem. 54 1989 1826 1831
37. Iodide 44 was not hydrolyzed under the reaction condition.
38. H. Miyabe, M. Ueda, N. Yoshioka, and T. Naito Synlett 1999 465 467
39. H. Miyabe, M. Ueda, N. Yoshioka, K. Yamakawa, and T. Naito Tetrahedron 56 2000 2413 2420
40. 3B, see: N. Kihara, C. Ollivier, and P. Renaud Org. Lett. 9 1999 1419 1422 and references cited therein
41. For radical-mediated iodoperfluoroalkylation reaction of α-methylene esters, see: (a) N. Kamigata, T. Fukushima, Y. Terakawa, M. Yoshida, and M. Iyoda J. Chem. Soc., Perkin Trans. 1 1991 627 633
42. Z.-M. Qui, and D.J. Burton J. Org. Chem. 60 1995 3465 3472 and references cited therein
43. A. Hayen, R. Koch, W. Saak, D. Haase, and J.O. Metzger J. Am. Chem. Soc. 122 2000 12458 12468
44. D.N. Harpp, L.Q. Bao, C.J. Black, J.G. Gleason, and R.A. Smith J. Org. Chem. 40 1975 3420 3427
45. I.P. Singh, K.E. Milligan, and W.H. Gerwick J. Nat. Prod. 62 1999 1333 1335
46. For the synthesis of (±)-tanikolide, see: (a) M.-Y. Chang, C.-L. Lin, and S.-T. Chen J. Chin. Chem. Soc. 48 2001 787 794
47. J. Krauss Nat. Prod. Lett. 15 2001 393 399
48. R. Zhang, Z. Wang, F. Wei, and Y. Huang Synth. Commun. 32 2002 2187 2194
49. H. Zhai, Q. Chen, J. Zhao, S. Luo, and X. Jia Tetrahedron Lett. 44 2003 2893 2894
50. For the synthesis of (+)-tanikolide, see: (e) A.E. Koumbis, K.M. Dieti, G. Vikentiou, and J.K. Gallos Tetrahedron Lett. 44 2003 2513 2516
51. T. Ohgiya, and S. Nishiyama Tetrahedron Lett. 45 2004 8273 8275
52. H. Arasaki, M. Iwata, M. Makida, and Y. Masaki Chem. Pharm. Bull. 51 2004 848 852
53. J.M. Schomaker, and B. Borhan Org. Biomol. Chem. 2 2004 621 624
54. Q. Chen, H. Deng, J. Zhao, Y. Lu, M. He, and H. Zhai Tetrahedron 61 2005 8390 8393 and references cited therein
55. G.W. Kabalka, K.A.R. Sastry, G.W. McCollum, and H. Yoshioka J. Org. Chem. 46 1981 4296 4298
56. J. Kagan, L. Tolentino, and M.G. Ettlinger J. Org. Chem. 40 1975 3085 3093
57. T. Yajima, K. Okada, and H. Nagano Tetrahedron 60 2004 5683 5693
58. K.B.G. Torsell, A.C. Hazell, and R.G. Hazell Tetrahedron 41 1985 5569 5575
59. Thijs, L.; Keltjens, R.; Ettema, G. J. B. U.S. Patent 2003073742, 2003; Chem. Abstr. 2003, 138, 321017.
60. O. Meth-Cohn, C. Moore, and H.C. Taljaard J. Chem. Soc., Perkin Trans. 1 1988 2663 2674