Enantioselective palladium-catalyzed total synthesis of vitamin E by employing a domino Wacker-Heck reaction

Chemistry - A European Journal

Volumn 12, Issue 34, 2006, Pages 8770-8776

  Tietze, Lutz F ^a   Stecker, Florian ^a   Zinngrebe, Julia ^a   Sommer, Konrad M ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Asymmetric catalysis; Domino reactions; Heck reactions; Palladium; Vitamins

Indexed keywords

CATALYSIS; CONDENSATION REACTIONS; HYDROGENATION; LITHIUM COMPOUNDS; PALLADIUM COMPOUNDS; VITAMINS;

CHIRAL CHROMAN 10; DOMINO REACTIONS; ENANTIOSELECTIVITY; METHYLLITHIUM; WACKER HECK REACTION;

CATALYSTS;

EID: 33845216121     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600849     Document Type: Article

References (60)

1. a) T. Netscher, Chimia 1996, 50, 563-567;
2. b) M. K. Horwitt, Am. J. Clin. Nutr. 1986, 44, 973-985;
3. c) H. M. Evans, K. S. Bishop, Science 1929, 56, 650-651.
4. a) G. T. Vatessary, W. E. Smith, H. T. Quach, Lipids 1989, 24, 1043-1047;
5. b) H. N. Jacobson, Free Radical Biol. Med. 1987, 3, 209-213;
6. c) G. W. Burton, A. Joyce, K. U. Ingold, Arch. Biochem. Biophys. 1983, 221, 281-290;
7. d) G. W. Burton, A. Joyce, K. U. Ingold, Lancet 1982, 2, 327;
8. e) J. E. Packer, T. F. Slater, R. L. Willson, Nature 1979, 278, 737-738;
9. f) E. J. Simon, C. S. Cross, A. T. Milhorat, J. Biol. Chem. 1956, 221, 797-805.
10. a) J. Kreimayer, M. Schmidt, Pharm. Ztg. 1998, 143, 823-828;
11. b) R. V. Acuff, R. G. Dunworth, L. W. Webb, J. R. Lane, Am. J. Clin. Nutr. 1998, 67, 459-464;
12. c) C. Kiyose, R. Maramatsu, Y. Kameyama, T. Ueda, O. Igarashi, Am. J. Clin. Nutr. 1997, 65, 785-789;
13. d) Ullmans Encyclopedia of Industrial Chemistry, Vol. A27 (Ed.; B. Elvers), Wiley-VCH, Weinheim, 1996, pp. 478-488;
14. e) K. U. Ingold, G. W. Burton, D. O. Foster, L. Hughes, D. A. Lindsay, A. Webb, Lipids 1987, 22, 163-172;
15. f) S. C. Cheng, G. W. Burton, K. U. Ingold, D. O. Foster, Lipids 1987, 22, 469-473.
16. W. Bonrath, T. Netscher, Appl. Catal. A 2005, 280, 55-73.
17. a) http ://www.cognis.com/veris/FactSheets/VERISFS_vitaminE_German.pdf;
18. b) P. P. Hoppe, G. Krennrich, Eur. J. Nutr. 2000, 39, 183-193;
19. c) D. H. Blatt, W. A. Pryor, J. E. Mata, R. Rodriguez-Proteau, J. Nutr. Biochem. 2004, 15, 380-395.
20. For some additional enantioselective approaches, see : a) B. M. Trost, H. C. Shen, L. Dong, J.-P. Surivet, C. Sylvain, J. Am. Chem. Soc. 2004, 126, 11966-11983;
21. b)B. M. Trost, N. Asakawa, Synthesis 1999, 1491-1494, and references therein;
22. c) L. F. Tietze, J. Görlitzer, A. Schuffenhauer, M. Hübner, Eur. J. Org. Chem. 1999, 1075-1080, and references therein;
23. d) B. M. Trost, F.D. Toste, J. Am. Chem. Soc. 1998, 120, 9074-9075;
24. e) L. F. Tietze, J. Görlitzer, Synthesis 1998, 873-878;
25. f) J. A. Hyatt, C. Skelton, Tetrahedron: Asymmetry 1997, 8, 523-526;
26. g) L. F. Tietze, J. Görlitzer, Liebigs Ann./Recl. 1997, 2221-2225;
27. h) L. F. Tietze, J. Görlitzer, Synlett 1997, 1049-1050;
28. L. F. Tietze, J. Görlitzer, Synthesis 1997, 877-885;
29. j) L. F. Tietze, J. Görlitzer, Synlett 1996, 11, 1041-1042;
30. k) L. F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851-5852;
31. H. Mayer, P. Schudel, R. Rüegg, O. Isler, Helv. Chim. Acta 1963, 46, 650-671.
32. L. F. Tietze, K. M. Sommer, J. Zinngrebe, F. Stecker, Angew. Chem. 2005, 117, 262-264;
33. Angew. Chem. Int. Ed. 2005, 44, 257-259.
34. a) L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006;
35. b) L. F. Tietze, H. Ila, H.P. Bell, Chem. Rev. 2004, 104, 3453-3516;
36. c) L. F. Tietze, A. Modi. Med. Res. Rev. 2000, 20, 304-322;
37. d) L. F. Tietze, F. Haunert in Stimulating Concepts in Chemistry (Eds. : F. Vögtle, J. F. Stoddart, M. Shibasaki), Wiley-VCH, Weinheim, 2000, pp. 39-64;
38. e) L. F. Tietze, M. E. Lieb, Curr. Opin. Chem. Biol. 1998, 2, 363-371;
39. f) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
40. g) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170;
41. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
42. a) A. B. Dounay, L. E. Overman, Chem. Rev. 2003, 103, 2945-2964;
43. b) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066;
44. c) A. de Meijere, E. F. Meyer in Metal-Catalyzed Cross-Coupling Reactions (Eds.; F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998;
45. d) M. Beller, T. H. Riermeir, G. Stark in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998.
46. a) H. Hocke, Y. Uozumi, Synlett 2002, 2049-2053;
47. b) T. Furutani, M. Hatsuda, R. Imashiro, M. Seki, Tetrahedron: Asymmetry 1999, 70, 4763-4768;
48. c) F. Dubois, M. Gingras, Tetrahedron Lett. 1998, 39, 5039-5040;
49. d) Y. Uozumi, K. Kato, T. Hayashi, J. Am. Chem. Soc. 1997, 119, 5063-5064;
50. e) M. B. Andrus, D. Asgari, J. A. Sclafani, J. Org. Chem. 1997, 62, 9365-9368;
51. f) Y. Uozumi, H. Kyota, E. Kishi, K. Kitayama, T. Hayashi, Tetrahedron: Asymmetry 1996, 7, 1603-1606;
52. g) T. D. Nelson, A. I. Meyers, J. Org. Chem. 1994, 59, 2655-2658;
53. h) J.-I. Kim, G. B. Schuster, J. Am. Chem. Soc. 1992, 114, 9309-9317;
54. A. Miyashita, H. Takaya, T. Souchi, R. Noyori, Tetrahedron 1984, 40, 1245-1253.
55. a) E. Mizuguchi, K. Achiwa, Chem. Pharm. Bull. 1997, 45, 1209-1211;
56. b) J. W. Scott, F. T. Bizzarro, D. R. Parrish, G. Saucy, Helv. Chim. Acta 1976, 59, 290-306.
57. L. Lombarde, Tetrahedron Lett. 1982, 23, 4293-4296.
58. I. Paterson, O. Delgado, G. J. Florence, I. Lyothier, J. P. Scott, N. Sereinig, Org. Lett. 2003, 5, 35-38.
59. S. Bell, B. Wüstenberg, S. Kaiser, F. Menges, T. Netscher, A. Pfaltz, Science 2006, 311, 642-644.
60. 3).