Traceless linkers for solid-phase synthesis. Homo- and hetero-Diels-Alder reactions of o-quinodimethanes

Synlett

Volumn , Issue 12, 1998, Pages 1381-1383

  Craig, Donald ^a   Robson, Michael J ^b   Shaw, Simon J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002424946     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1968     Document Type: Article

References (28)

1. Cleavage from the resin of products from solid-phase synthesis usually leaves a polar residue, most often hydroxyl or -NH, on the cleaved molecule. 'Traceless' cleavage avoids the generation of such polar functionalities.
2. Gowravaram, M. R.; Gallop, M. A. Tetrahedron Lett. 1997, 38, 6973;
3. Whitehouse, D. L.; Nelson K. H.; Savinov, S. N.; Austin, D. J. Tetrahedron Lett. 1997, 38, 7139;
4. Tietze, L. F.; Steinmetz, A. Synlett 1996, 667;
5. Gordon, D. W.; Steele, J. BioMed. Chem. Lett. 1995, 5, 47.
6. Johnson, C. R.; Zhang, B. Tetrahedron Lett. 1995, 36, 9253;
7. Hughes, I. Tetrahedron Lett. 1996, 37, 7595;
8. Nicolaou, K. C.; Pastor, J.; Winssinger, N.; Murphy, F. J. Am. Chem. Soc. 1998, 120, 5132.
9. Woolard, F. X.; Paetsch, J.; Ellman, J. A. J. Org. Chem 1997; 62, 6102.
10. Newlander, K. A.; Chenera, B.; Veber, D. F.; Yim, N. C. F.; Moore, M. L. J. Org. Chem. 1997, 62, 6726;
11. Hone, N. D.; Davies S. G.; Devereux, N. J.; Taylor, S. L.; Baxter, A. D. Tetrahedron Lett. 1998, 39, 897.
12. Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett. 1996, 37, 6491.
13. Zhao, X.; Jung, K. W.; Janda, K. D. Tetrahedron Lett. 1997, 38, 977;
14. Zhao, X.; Janda, K. D. Tetrahedron Lett. 1997, 38, 5437.
15. Van Marseveen, J. H.; den Hartog, J. A. J.; Engelen, V.; Visser, G.; Kruse, C. G. Tetrahedron Lett. 1996, 37, 8249;
16. Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143.
17. For an early example, see: Yedidia, V.; Leznoff, C. C.; Can. J. Chem. 1980, 58, 1144.
18. Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873.
19. 4 reduction of benzocyclobutenone, prepared according to a literature procedure: South, M. S.; Liebeskind, L. S.; J. Org. Chem. 1982, 47, 3815.
20. Wessel, H.-P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans 1 1985, 2247.
21. Burdick, D. J.; Struble, M. E.; Burnier, J. P. Tetrahedron Lett. 1993, 34, 2589.
22. Triflic acid was added as a solution in hexane (see below). The use of neat TfOH led to darkening of the polystyrene beads and decomposition.
23. Yields throughout are calculated from the amount of recovered 1 in the first step.
24. Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733.
25. Prior to the solid-phase studies, solution-phase model reactions were carried out using the benzyl ether of 1. Cycloadducts were obtained in good yields in all cases.
26. Compound 6b exhibited a 7% n.O.e.between the methyl group and the nitrophenyl benzylic methine proton; we thank Mr Dick Sheppard and Mr Paul Hammerton of this department for this determination. The structure of compound 6c was confirmed by X-ray crystallography; we thank Professor David Williams and Dr Andrew White of this department for this determination.
27. Compound 6h exhibited no n.O.e.between the methyl group and the nitrophenyl benzylic methine proton; we thank Mr Dick Sheppard and Mr Paul Hammerton of this department for this determination.
28. +, 287.1396).