Synthesis and applications of tert-alkoxysiloxane linkers in solid-phase chemistry

Tetrahedron

Volumn 63, Issue 2, 2007, Pages 299-311

  Meloni, Marco M ^a   White, Peter D ^b   Armour, Duncan ^c   Brown, Richard C D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b Merck Biosciences Ltd   (United Kingdom)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CHLORINE DERIVATIVE; PHENOL DERIVATIVE; RESIN; SILOXANE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS;

EID: 33751532367     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.052     Document Type: Article

References (64)

1. Jarowicki K., and Kocienski P. J. Chem. Soc., Perkin Trans. 1 (2001) 2109-2135
2. Kocienski P.J. Protecting Groups (1994), Georg Thieme, Stuttgart
3. Wuts P.G.M., and Greene T.W. Protective Groups in Organic Synthesis. 3rd ed. (1999), Wiley, New York, NY
4. For selected linker reviews, see:
5. Wills A.J., and Balasubramanian S. Curr. Opin. Chem. Biol. 7 (2003) 346-352
6. James I.W. Tetrahedron 55 (1999) 4855-4946
7. Guillier F., Orain D., and Bradley M. Chem. Rev. 100 (2000) 2091-2157
8. For some reviews of solid-phase synthesis and combinatorial chemistry, see:
9. Balkenhohl F., von dem Bussche-Hünnefeld C., Lansky A., and Zechel C. Angew. Chem., Int. Ed. 35 (1996) 2289-2337
10. Brown R.C.D. J. Chem. Soc., Perkin Trans. 1 (1998) 3293-3320
11. Dolle R.E. J. Comb. Chem. 6 (2004) 623-679
12. Thompson L.A., and Ellman J.A. Chem. Rev. 96 (1996) 555-600
13. Chan T.H., and Huang W.Q. J. Chem. Soc., Chem. Commun. (1985) 909-910
14. Randolph J.T., McClure K.F., and Danishefsky S.J. J. Am. Chem. Soc. 117 (1995) 5712-5719
15. Nakamura K., Ishii A., Ito Y., and Nakahara Y. Tetrahedron 55 (1999) 11253-11266
16. Thompson L.A., Moore F.L., Moon Y.C., and Ellman J.A. J. Org. Chem. 63 (1998) 2066-2067
17. Paterson I., Donghi M., and Gerlach K. Angew. Chem., Int. Ed. 39 (2000) 3315-3319
18. Lindsley C.W., Chan L.K., Goess B.C., Joseph R., and Shair M.D. J. Am. Chem. Soc. 122 (2000) 422-423
19. Hijikuro I., Doi T., and Takahashi T. J. Am. Chem. Soc. 123 (2001) 3716-3722
20. Chenera B., Finkelstein J.A., and Veber D.F. J. Am. Chem. Soc. 117 (1995) 11999-12000
21. Plunkett M.J., and Ellman J.A. J. Org. Chem. 60 (1995) 6006-6007
22. Brown S.D., and Armstrong R.W. J. Org. Chem. 62 (1997) 7076-7077
23. Schuster M., Lucas N., and Blechert S. Chem. Commun. (1997) 823-824
24. Lee Y., and Silverman R.B. Org. Lett. 2 (2000) 3743-3746
25. Gu W., Liu S., and Silverman R.B. Org. Lett. 4 (2002) 4171-4174
26. Gu W., and Silverman R.B. J. Org. Chem. 68 (2003) 8774-8779
27. Lipshutz B.H., and Shin Y.J. Tetrahedron Lett. 42 (2001) 5629-5633
28. Mullen D.G., and Barany G. J. Org. Chem. 53 (1988) 5240-5248
29. Chao H.G., Bernatowicz M.S., Reiss P.D., Klimas C.E., and Matsueda G.R. J. Am. Chem. Soc. 116 (1994) 1746-1752
30. Routledge A., Stock H.T., Flitsch S.L., and Turner N.J. Tetrahedron Lett. 47 (1997) 8287-8290
31. Farrall M.J., and Fréchet J.M.J. J. Org. Chem. 41 (1976) 3877-3882
32. Recently a tert-butyldiarylsilyl linker was prepared from metallated polystyrene, see:. DiBlasi C.M., Macks D.E., and Tan D.S. Org. Lett. 7 (2005) 1777-1780
33. Stöver H.D.H., Lü P.Z., and Fréchet J.M.J. Polym. Bull. 25 (1991) 575-582
34. Stranix B.R., Liu H.Q., and Darling G.D. J. Org. Chem. 62 (1997) 6183-6186
35. Hu Y., Porco J.A.J., Labadie J.W., Gooding O.W., and Trost B.M. J. Org. Chem. 63 (1998) 4518-4521
36. Smith E.M. Tetrahedron Lett. 40 (1999) 3285-3288
37. For an example of direct silylether formation from a polymer-bound silane, see:. Hu Y., and Porco J.A.J. Tetrahedron Lett. 39 (1998) 2711-2714
38. Savin K.A., Woo J.C.G., and Danishefsky S.J. J. Org. Chem. 64 (1999) 4183-4186
39. Routledge A., Wallis M.P., Ross K.C., and Fraser W. Bioorg. Med. Chem. Lett. 5 (1995) 2059-2064
40. Paterson I., and Temal-Laïb T. Org. Lett. 4 (2002) 2473-2476
41. Gillard J.W., Fortin R., Morton H.E., Yoakim C., Quesnelle C.A., Daignault S., and Guindon Y. J. Org. Chem. 53 (1988) 2602-2608
42. Guindon Y., Fortin R., Yoakim C., and Gillard J.W. Tetrahedron Lett. 25 (1984) 4717-4720
43. For a preliminary communication of this work, see:. Meloni M.M., Brown R.C.D., White P.D., and Armour D. Tetrahedron Lett. 43 (2002) 6023-6026
44. It is possible that the spot observed on the TLC plate could be silanol or another silicon derivative formed by hydrolysis of the chlorosiloxane.
45. Hernandez A.S., and Hodges J.C. J. Org. Chem. 62 (1997) 3153-3157
46. Successful formation of the 3° alcohol resin could be confirmed by the methyl red test, see:. Burkett B.A., Brown R.C.D., and Meloni M.M. Tetrahedron Lett. 42 (2001) 5773-5775
47. For reviews describing solid-phase Pd-catalysed C-C bond formation, see:
48. Bräse S., Kirchhoff J.H., and Köbberling J. Tetrahedron 59 (2003) 885-939
49. Lorsbach B.A., and Kurth M.J. Chem. Rev. 99 (1999) 1549-1581
50. Sammelson R.E., and Kurth M.J. Chem. Rev. 101 (2001) 137-202
51. Salvatore R.N., Yoon C.H., and Jung K.W. Tetrahedron 57 (2001) 7785-7811
52. Albericio F., and Kates S.A. Coupling methods: Solid-phase formation of amide and ester bonds. In: Kates S.A., and Albericio F. (Eds). Solid Phase Synthesis (2000), Marcel Dekker, New York, NY 275-330
53. For imine formation, see:. Look G.C., Murphy M.M., Campbell D.A., and Gallop M.A. Tetrahedron Lett. 36 (1995) 2937-2940
54. Chen X., Hortelano E.R., Eliel E.L., and Frye S.V. J. Am. Chem. Soc. 114 (1992) 1778-1784
55. Kabalka G.W., Shoup T.M., and Goudgaon N.M. J. Org. Chem. 54 (1989) 5930-5933
56. Mikami K., Terada M., and Nakai T. J. Am. Chem. Soc. 112 (1990) 3949-3954
57. Schmidt B., and Pohler M. Org. Biomol. Chem. 1 (2003) 2512-2517
58. Berteina S., Wendeborn S., Brill W.K.D., and De Mesmaeker A. Synlett (1998) 676-678
59. Grether U., and Waldmann H. Chem.-Eur. J. 7 (2001) 959-971
60. Wendeborn S., Berteina S., Brill W.K.D., and De Mesmaeker A. Synlett (1998) 671-675
61. Katritzky A.R., Rogovoy B.V., Vvedensky V., Kovalenko K., and Forood B. J. Comb. Chem. 4 (2002) 290-294
62. Sarin V.K., Kent S.B.H., Tam J.P., and Merrifield R.B. Anal. Biochem. 117 (1981) 147-157
63. Doi T., Iijikuro I., and Takahashi T. Synlett (1999) 1751-1753
64. Vojkovsky T. Pept. Res. 8 (1995) 236-237