A highly acid labile silicon linker for solid phase synthesis

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 897-900

  Hone, Neal D ^a   Davies, Stephen G ^b   Devereux, Nicholas J ^a   Taylor, Sara L ^a   Baxter, Anthony D ^a  

^a A Division of Oxford Asymmetry Ltd   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; ARYLSILANE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN; SOLID PHASE EXTRACTION; TECHNIQUE;

EID: 0032546094     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10650-5     Document Type: Article

References (22)

1. 1. For recent reviews see (a) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173
2. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600
3. (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
4. 2. Wang, S, -W, J. Am. Chem. Soc., 1973, 95, 1328-1333.
5. 3. Rink, H, Tetrahedron Lett., 1987, 28, 3787-3790.
6. 4. Thompson, L. A.; Ellman, J. A., Tetrahedron Lett., 1994, 35, 9333-9336.
7. 5. (a) Ho, C. Y.; Kukla, M. J., Tetrahedron Lett., 1997, 38, 2799-2802
8. (b) Hauske, J. R.; Dorff, P., Tetrahedron Lett., 1995, 36, 1589-1592.
9. 6. (a) Chenera, B.; Finkelstein, J. A. ; Veber, D. F. J. Am. Chem. Soc., 1995, 117, 11999-12000
10. (b) Plunkett, M. J.; Ellman, J. A. J. Org. Chem., 1995, 60, 6006-6007
11. (c) Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett., 1996, 37, 2703-2706.
12. 7. Monolithiation of 1,4-dibromobenzene using one equivalent of n-BuLi in THF at -78 °C for 1 h, followed by treatment with one equivalent of chloromethyldimethylchlorosilane provided chloromethydimethyl-4-bromophenylsilane. This reagent was converted to 1a following ref. 8.
13. 8. Sommer, L. H.; Goldberg, G. M.; Barnes, G. H.; Stone, L. S. J. Am. Chem. Soc., 1954, 76, 1609-1612.
14. 9. Frenette, R.; Friesen, R. W. Tetrahedron Lett., 1994, 35, 9177-9180.
15. max (approx. 260 nm) approached the limits of detection in TFA and could not be accurately determined.
16. 11. (a) Eaborn, C. J. Organometal Chem., 1975, 100, 43-57.
17. (b) Eaborn, C.; Bott, R. W. in MacDiarmid, A. G., (Ed.) Organometallic Compounds of the Group IV Elements, Vol. 1, Pt. 1, Marcel Dekker, New York, 1968, p. 407-431.
18. 12. Deshpande, M. S. Tetrahedron Lett., 1994, 35, 5613-5614.
19. 4, toluene, Δ), saponification and TBTU mediated coupling to aminomethyl polystyrene.
20. 14. Cyclopropylamine, 2,2,2-trifluoroethylamine, 1-(3-aminopropyl)-2-pipecoline and 4-methylbenzylamine.
21. 15. Morpholine-4-carbonyl chloride, thiophene-2-carbonyl chloride, isoxazole-5-carbonyl chloride, 4-bromophenyl isocyanate and 1-methylimidazole-4-sulphonyl chloride.
22. +.