Synthesis of novel C2 symmetrical and enantiomerically pure thiepines

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 813-816

  Hudson, Andrew ^a   Orpen, A Guy ^a   Phetmung, Hirihattaya ^a   Wyatt, Paul ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

THIEPIN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; SYNTHESIS;

EID: 0033593535     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02460-5     Document Type: Article

References (19)

1. Eames, J.; Kuhnert, N.; Jones, R. V. H.; Warren, S., Tetrahedron Lett., 1998, 39, 1247-1250.
2. Cerè, V.; Peri, F.; Pollicino, S., J. Org. Chem., 1997, 8572-8574.
3. Solladié-Cavallo, A.; Adib, A., Tetrahedron, 1992, 48, 2453-2464.
4. Aggarwal, V. K.; Kalomiri, M.; Thomas, A. P., Tetrahedron: Asymmetry, 1994, 5, 723-730.
5. The same diastereomer and same enantiomer.
6. Kuszmann, J.; Sohar, P., Carbohydr. Res., 1977, 56, 105-115.
7. Breau, L.; Ogilvie, W. W.; Durst, T., Tetrahedron Lett., 1990, 31, 35-38.
8. Previously prepared in racemic form together with its meso diastereomer: Nógrádi, M.; Ollis, W. D.; Sutherland, I. O., J. Chem. Soc., Perkin Trans. 1, 1974, 621-624.
9. Warren, S.; Wyatt, P., Tetrahedron: Asymmetry, 1996, 7, 989-992.
10. Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S., J. Org. Chem., 1977, 42, 384-387.
11. The determination of enantiomeric excess was made in comparison with a racemic sample.
12. Chiralcel OD column with heptane/iso-propanol
13. For an example of an ortho-lithiation and an α-lithiation used together to form a heterocycle see Hartman, G. D.; Halczenko, W., Tetrahedron Lett., 1987, 28, 3241-3244.
14. 2 symmetric, the sulfoxide is not
15. Fehér, F.; Degen, B., Angew. Chem., Int. Edn. Engl., 1967, 6, 703-704.
16. Banerji, A.; Kalena, G. P., Tetrahedron Lett., 1980, 21, 3003-304.
17. Sundberg, J., J. Heterocycl. Chem., 1977, 14, 517-518.
18. Warren, S.; Wyatt, P.; McPartlin, M.; Woodroffe, T., Tetrahedron Lett., 1996, 37, 5609-5612.
19. Trost, B. M.; Bogdanowicz, M. J., J. Am. Chem. Soc., 1973, 95, 5298-5307.