Enantioselective synthesis of the chromane moiety of vitamin E

European Journal of Organic Chemistry

Volumn , Issue 5, 1999, Pages 1075-1084

  Tietze, Lutz F ^a   Görlitzer, Jochen ^a   Schuffenhauer, Ansgar ^a   Hübner, Matthias ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Asymmetric synthesis; Atropisomerism; Bis(hydroxylation); Conformational analysis; Palladium; Vitamin E

Indexed keywords

ALPHA TOCOPHEROL DERIVATIVE; PALLADIUM;

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG HYDROXYLATION; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION;

EID: 0344980331     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199905)1999:5<1075::AID-EJOC1075>3.0.CO;2-I     Document Type: Article

References (56)

1. [1a] L. J. Machlin, "Vitamin E" in Handbook of Vitamins, 2nd ed. (Ed.: L. J. Machlin), Marcel Dekker Inc., New York, 1991, p. 99-144.
2. [1b] G. W. Burton, K. U. Ingold, J. Am. Chem. Soc. 1981, 103, 6412-6477.
3. T. Netscher, Chimia 1996, 50, 563-567.
4. [3a] E. Mizugushi, T. Suzuki, K. Achiwa, Synlett 1994, 929-930.
5. [3b] N. Cohen, J. W. Scott, F. T. Bizzaro, R. J. Lopresti, W. F. Eichel, G. Saucy, Helv. Chim. Acta 1978, 61, 837-843.
6. [3c] J. W. Scott, F. T. Bizzaro, D. R. Parrish, G. Saucy, Helv. Chim. Acta 1976, 59, 290-306.
7. [3d] J. A. Hyatt, C. Skelton, Tetrahedron: Asymmetry 1997, 8, 523-526.
8. [4a] J. Hübscher, R. Barner, Helv. Chim. Acta 1990, 73, 1068-1086.
9. [4b] Y. Sakito, G. Suzukamo, Tetrahedron Lett. 1982, 23, 4953-4954.
10. [5a] R. Barner, M. Schmid, Helv. Chim. Acta 1979, 62, 2384-2399.
11. [5b] N. Cohen, R. J. Lopresti, G. Saucy, J. Am. Chem. Soc. 1979, 101, 6710-6716.
12. [6a] L. F. Tietze, J. Görlitzer, Synthesis 1998, 873-878.
13. [6b] L. F. Tietze, J. Görlitzer, Liebigs Ann. 1997, 2221-2225.
14. [6c] L. F. Tietze, J. Görlitzer, Synlett 1997, 1049-1050.
15. [6d] L. F. Tietze, J. Görlitzer, Synthesis 1997, 873-878.
16. [6e] L. F. Tietze, J. Görlitzer, Synlett 1996, 1041-1042.
17. [6f] E. Mizuguchi, K. Achiwa, Synlett 1995, 1255-1056.
18. [6g] S. Takano, T. Sugihara, K. Ogasawara, Synlett 1990, 451-452.
19. [6h] K. Takabe, K. Okisaka, Y. Uchiyama, T. Katagiri, H. Yoda, Chem. Lett. 1985, 561-562.
20. [7a] D. W. Nelson, A. Gypser, P. T. Ho, H. C. Kolb, T. Kondo, H.-L. Kwong, D. V. McGrath, A. E. Rubin, P.-O. Norrby, K. P. Gable, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 1840-1858.
21. [7b] H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
22. [8a] L. F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851-5852.
23. [8b] L. F. Tietze, K. Schiemann, C. Wegner, C. Wulff, Chem. Eur. J. 1996, 2, 1164-1172.
24. [8c] L. F. Tietze, C. Wegner, C. Wulff, Synlett 1996, 471-472.
25. [8d] L. F. Tietze, C. Wulff, C. Wegner, A. Schuffenhauer, K. Schiemann, J. Am. Chem. Soc. 1998, 120, 4276-4280.
26. [8e] L. F. Tietze, C. Wegner, C. Wulff, Eur. J. Org. Chem. 1998, 1639-1644.
27. H. Suzuki, Org. Synth. Coll. Vol. 1988, 6, 700-701.
28. [10a] K. Sonogashira, Y. Thoda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467-4470.
29. [10b] R. Rossi, A. Carpita, F. Bellina, Org. Prep. Proc. Int. 1995, 27, 127-160.
30. E. M. Burgess, H. R. Penton Jr., E. A. Taylor, J. Org. Chem. 1973, 38, 26-31.
31. J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549.
32. [13a] D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4156-4159.
33. [13b] D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
34. [13c] R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899-2903.
35. W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele. M. Beller, Chem. Eur. J. 1997, 3, 1357-1364.
36. [15a] C. Lilibris, B. Resul, U. Hacksell, Tetrahedron 1995, 51, 9139-9154.
37. [15b] J.-M. Gaudin, Tetrahedron Lett. 1991, 32, 6113-6116.
38. L. F. Tietze, J. Görlitzer, unpublished results.
39. D. J. Ager, Synthesis 1984, 384-398.
40. L. F. Tietze, A. Schuffenhauer, J. Görlitzer, unpublished results.
41. See, for example: [19a] H.-S. Byun, E. R. Kumar, R. Bittman, J. Org. Chem. 1994, 59, 2630-2633.
42. [19b] C. Vilcheze, R. Bittman J. Lipid Res. 1994, 35, 734-738.
43. [19c] E. J. Corey, A. Guzman-Perez, M. C. Noe, J. Am. Chem. Soc. 1995, 117, 10805-10816.
44. [19d] E. J. Corey, A. Guzman-Perez, M. Noe, Tetrahedron Lett. 1995, 36, 3481-3484.
45. Z.-M. Wang, X.-L. Zhang, K. B. Sharpless, Tetrahedron Lett. 1993, 34, 2267-2270.
46. [21a] L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
47. [21b] U. Beifuss, L. F. Tietze, Angew. Chem. Int. Ed. Engl. 1993, 32, 131-170.
48. [22a] I. Petterson, U. Berg, J. Chem. Res (S) 1984, 208-209.
49. [22b] J. E. Anderson, Tetrahedron 1987, 43, 3041-3046.
50. [22c] C. S. C. Yang, R. S. H. Liu, Tetrahedron Lett. 1973, 14, 4811-4814.
51. [22d] J. E. Anderson, D. J. D. Barkel, C. J. Cooksey, Tetrahedron Lett. 1983, 24, 1077-1080.
52. [23a] D. S. Stephenson, G. Binsch, J. Magn. Reson. 1978, 32, 145-152.
53. [23b] D. S. Stephenson, G. Binsch, Quantum Chem. Progr. Exch. 1978, 11, 365.
54. G. Binsch, H. Kessler, Angew. Chem. Int. Ed. Engl. 1980, 19, 411-428.
55. [25a] The PM3 calculations were performed with a PC using a 32-bit version of the program package MOPAC 6.0 by J. J. P. Stewart, 1990.
56. [25b] J. J. P. Stewart, J. Comp. Chem. 1989, 10, 108.