Desilylation procedure via a naphthalene-catalysed lithiation reaction

Tetrahedron

Volumn 61, Issue 28, 2005, Pages 6908-6915

  Behloul, Cherif ^a   Guijarro, David ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Alcohols; Amines; Deprotection; Desilylation; Lithium; Naphthalene; Silyl; Thiols

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; LITHIUM DERIVATIVE; NAPHTHALENE DERIVATIVE; PHENYL GROUP; TETRAHYDROFURAN DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DEPROTECTION REACTION; DESILYLATION; HYDROLYSIS; LITHIATION; LOW TEMPERATURE; POWDER; PRIORITY JOURNAL; RACEMIZATION; STEREOCHEMISTRY;

EID: 20444435438     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.145     Document Type: Article

References (58)

1. (a) Kunz, H.; Waldmann, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, pp 652-657.
2. K. Jarowicki, and P. Kocienski Contemp. Org. Synth. 3 1996 397 431
3. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 1999 Wiley New York 113 148 pp 273-276
4. J. Robertson Protecting Group Chemistry 2000 Oxford University Press Oxford 74 79
5. J.D. White, and R.G. Carter I. Fleming Science of Synthesis Vol. 4 2002 Thieme Stuttgart 371 412
6. P.J. Kocienski Protecting Groups 2004 Thieme Stuttgart 188 230
7. (a) Ref. 1c, p 600. (b) Ref. 1d, p 81. (c) Ref. 1e, pp 451-472. (d) Ref. 1f, pp 595-599.
8. (a) Ref. 1c, p. 482. (b) Ref. 1e, pp 427-432.
9. T.D. Nelson, and R.D. Crouch Synthesis 1996 1031 1069
10. M. Schelhaas, and H. Waldmann Angew. Chem., Int. Ed. Engl. 35 1996 2056 2083
11. R.D. Crouch Tetrahedron 60 2004 5833 5871
12. See, for instance: (a) J.H. Clark Chem. Rev. 80 1980 429 452
13. S.J. Shimshock, R.E. Watermire, and P. Deshong J. Am. Chem. Soc. 113 1991 8791 8796
14. See, for instance: E.W. Collington, H. Finch, and I.J. Smith Tetrahedron Lett. 26 1985 681 684
15. K. Toshima, K. Yanagawa, S. Mukaiyama, and K. Tatsuta Tetrahedron Lett. 31 1990 6697 6698
16. K. Lee, and D.F. Wiemer J. Org. Chem. 58 1993 7808 7812
17. J.F. Cormier, M.B. Isaac, and L.-F. Chen Tetrahedron Lett. 34 1993 243 246
18. D. Rotulo-Sims, and J. Prunet Org. Lett. 4 2002 4701 4704
19. For reviews, see: (a) M. Yus Chem. Soc. Rev. 25 1996 155 161
20. D.J. Ramoǐn, and M. Yus Eur. J. Org. Chem. 2000 225 237
21. M. Yus Synlett 2001 1197 1205
22. M. Yus, and D.J. Ramoǐn Latv. J. Chem. 2002 79 92
23. D.J. Ramoǐn, and M. Yus Rev. Cubana Quim. 14 2002 75 115
24. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rapport, Z., Mareck, I., Eds.; Wiley: Chichester, 2004, Chapter 11.
25. For a mechanistic study, see: (g) M. Yus, R.P. Herrera, and A. Guijarro Tetrahedron Lett. 42 2001 3455 3458
26. M. Yus, R.P. Herrera, and A. Guijarro Chem. Eur. J. 8 2002 2574 2584
27. R.P. Herrera, A. Guijarro, and M. Yus Tetrahedron Lett. 44 2003 1309 1312
28. For a polymer-supported version of this reaction, see: (a) C. Goǐmez, S. Ruiz, and M. Yus Tetrahedron Lett. 39 1998 1397 1400
29. C. Goǐmez, S. Ruiz, and M. Yus Tetrahedron 55 1999 7017 7026
30. M. Yus, C. Goǐmez, and P. Candela Tetrahedron 58 2002 6207 6210
31. P. Candela, C. Gomez, and M. Yus Russ. J. Org. Chem. 40 2004 795 801
32. For a review, see: D. Guijarro, and M. Yus Recent Res. Dev. Org. Chem. 2 1998 713 744
33. For reviews, see: (a) C. Naǐjera, and M. Yus Trends Org. Chem. 2 1991 155 181
34. C. Naǐjera, and M. Yus Recent Res. Dev. Org. Chem. 1 1997 67 96
35. C. Naǐjera, and M. Yus Curr. Org. Chem. 7 2003 867 926
36. C. Naǐjera, J.M. Sansano, and M. Yus Tetrahedron 59 2003 9255 9303
37. R. Chinchilla, C. Naǐjera, and M. Yus Chem. Rev. 2004 2667 2722
38. For reviews, see: (a) M. Yus, and F. Foubelo Rev. Heteroatom Chem. 17 1997 73 107
39. M. Yus, and F. Foubelo Targets Heterocycl. Syst. 6 2002 136 171
40. M. Yus Pure Appl. Chem. 75 2003 1453 1475
41. E. Alonso, D.J. Ramoǐn, and M. Yus Tetrahedron 53 1997 14355 14368
42. M. Yus, C. Behloul, and D. Guijarro Synthesis 2003 2179 2184
43. C. Behloul, D. Guijarro, and M. Yus Synthesis 2004 1274 1280
44. In a previous study, we found that 1-[tert-butyl(diphenyl)silyloxy] docosane did not give the desilylation product after 12 h at room temperature. See Ref. 13.
45. E. Alonso, D. Guijarro, and M. Yus Tetrahedron 51 1995 11457 11464
46. M. Yus, P. Martínez, and D. Guijarro Tetrahedron 57 2001 10119 10124
47. S.C. Watson, and J.F. Eastham J. Organomet. Chem. 9 1967 165 168
48. S.J. Monger, D.M. Parry, and S.M. Roberts J. Chem. Soc., Chem. Commun. 1989 381 382
49. J.M. Blackwell, K.L. Foster, V.H. Beck, and W.E. Piers J. Org. Chem. 64 1999 4887 4892
50. S.A. Hardinger, and N. Wijaya Tetrahedron Lett. 34 1993 3821 3824
51. S.U. Son, S.-J. Paik, and Y.K. Chung J. Mol. Catal. A: Chem. 151 2000 87 90
52. M. Fujita, and T. Hiyama J. Org. Chem. 53 1988 5405 5415
53. T. Chan, and W. Huang Huaxue Xuebao 44 1986 934 939
54. Chem. Abstr. 107 1986 39463
55. C.R. Lucas, M.J. Newlands, E.J. Gabe, and F.L. Lee Can. J. Chem. 65 1987 898 902
56. A similar procedure for the synthesis of silyl ethers has been published. See Ref. 21.
57. The ester was prepared using the method 1 described in page 2373 of the following article: B.M. Trost, J.L. Belletire, S. Godleski, P.G. McDougal, J.M. Balkovec, J.J. Baldwin, M.E. Christy, G.S. Ponticello, S.L. Varga, and J.P. Springer J. Org. Chem. 51 1986 2370 2374
58. 1H NMR spectra, but we could not use them to determine the optical purity of product (R)-1c due to partial collapse of the signals of the two diastereomeric esters obtained from racemic 2-octanol.