The phenylthiocyclopropylsilyl group: A useful latent hydroxy group

Tetrahedron

Volumn 56, Issue 14, 2000, Pages 2025-2036

  Angelaud, Rémy ^a   Landais, Yannick ^a,b  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Oxidation; Pummerer reactions; Silicon and compounds; Sulfoxides

Indexed keywords

HYDROXYL GROUP;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034737485     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00112-5     Document Type: Article

References (54)

1. (a) Tamao, K.; Ishida, N.; Tanaka, P.; Kumada, M. Organometallics 1983, 2, 1694-1696.
2. (b) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37-C39.
3. (c) Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29-31.
4. (d) Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317-337.
5. (a) Fleming, I. Chemtracts: Org. Chem. 1996, 1-64.
6. (b) Landais, Y.; Jones, G. Tetrahedron 1996, 52, 7599-7662.
7. (c) Tamao, K. In Advances in Silicon Chemistry, Jai Press Inc., 1996; Vol. 3, pp 1-62.
8. For recent reports addressing this problem, see: (a) Itami, K.; Mitsudo, K.; Yoshida, J.-I. Tetrahedron Lett. 1999, 40, 5537-5540.
9. (b) Groaning, M. D.; Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1998, 63, 5517-5522.
10. (c) Knölker, H. J.; Jones, P. G.; Wanzl, G. Synlett, 1998, 613-616.
11. (d) Shaw, J. T.; Woerpel, K. A. Tetrahedron 1997, 53, 16597-16606.
12. (d) Fleming, I.; Winter, S. B. D. Tetrahedron Lett. 1995, 36, 1733-1734.
13. Angelaud R., Landais Y., Maignan C. Tetrahedron Lett. 36:1995;3861-3864.
14. (a) Oae, S.; Numata, T. The Pummerer type of reactions. In Isotopes in Organic Synthesis; Buncel, E., Lee, C. C., Eds.; Elsevier: New York, 1980; Vol. 5, chap. 2.
15. (b) Ager, D. J. Tetrahedron Lett. 1980, 21, 4759-4762.
16. (a) Bhupathy, M.; Cohen, T. Tetrahedron Lett. 1987, 28, 4793-4796.
17. (b) Bhupathy, M.; Cohen, T. Tetrahedron Lett. 1987, 28, 4797-4800.
18. For a review on superbases, see: Schlosser, M. Organoalkali reagents. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994; pp 1-166.
19. Lohray B.B. Synthesis. 1992;1035-1052.
20. (a) Chan, T. H.; Labrecque, D. Tetrahedron Lett. 1992, 33, 7997-8000.
21. (b) Li, L.-H.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1991, 32, 2879-2882.
22. (c) Tamao, K.; Nakajo, E.; Ito, Y. Synth. Commun. 1987, 17, 1637-1646.
23. (d) Muchowski, J. M.; Naef, R.; Maddox, L. Tetrahedron Lett. 1985, 26, 5375-5378.
24. (a) Hoppe, D.; Hintze, H.; Tebben, P.; Paetow, M.; Ahrens, H.; Schwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarnieri, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure Appl. Chem. 1994, 66, 1479-1486.
25. (b) Beak, P.; Du, H. J. Am. Chem. Soc. 1993, 115, 2516-2518.
26. (c) Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342-12343.
27. A report by van Boom et al. led to sensibly opposite conclusions. Their studies on the closely related dimethyl(phenylthio)methylsilyl group indicate that its oxidation into the alcohol did not proceed through sila-Pummerer rearrangement but rather by direct displacement of the sulfoxide group by fluoride as demonstrated by the recovery of phenylmethylsulfoxide: (a) van Delft, F. L.; van der Marel, G. A.; van Boom, J. H. Synlett 1995, 1069-1070.
28. (b) van Delft, F. L. PhD Thesis, University of Leiden, 1996.
29. Magar S.S., Desai R.C., Fuchs P.L. J. Org. Chem. 57:1992;5360-5369.
30. Miklos P., Senning A. Tetrahedron. 43:1987;249-254.
31. Ojima I., Kumagai M. J. Organomet. Chem. 157:1978;359-372.
32. Kolb H.C., VanNieuwenhze M.S., Sharpless K.B. Chem. Rev. 94:1994;2483-2547.
33. Fuganti C., Grasselli P., Servi S., Lazzarani A., Casati P. Tetrahedron. 44:1988;2575-2582.
34. For a review on Sharpless asymmetric amino-hydroxylation, see: O'Brien, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 326-329.
35. N-haloamides and carbamates have been used as electrophilic nitrogen sources in the preparation of sulfilimines, see: (a) Tomooka, C. S.; LeCloux, D. D.; Sasaki, H.; Carreira, E. M. Org. Lett. 1999, 1, 149-152.
36. (b) Celentano, G.; Colonna, S.; Gaggero, N.; Richelmi, C. J. Chem. Soc., Chem. Commun. 1998, 701-702.
37. (c) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015-5016.
38. (d) Genêt, J.-P.; Mallart, S.; Greck, C.; Piveteau, E. Tetrahedron Lett. 1991, 32, 2359-2362.
39. Abd.Rahman N., Fleming I. Synth. Commun. 23:1993;1583-1594.
40. Maruoka K., Fukutani Y., Yamamoto H. J. Org. Chem. 50:1985;4412-4414.
41. The irreproducibility of the cyclopropanation reaction was attributed to the presence of the thioether group known to generate sulfur ylides in the presence of carbenoid species, see: Kosarych, Z.; Cohen, T. Tetrahedron Lett. 1982, 23, 3019-3022.
42. Morikawa T., Sasaki H., Hanai R., Shibuya A., Taguchi T. J. Org. Chem. 59:1994;97-103.
43. Larson G.L., Klesse R., Cartledge F.K. Organometallics. 6:1987;2250-2252.
44. Tamao K., Nagata K., Ito Y., Maeda K., Shiro M. Synlett. 1994;257-259.
45. Landais Y. Main Group Chemistry News. 5:1997;4-13.
46. Bulugahapitiya P., Landais Y., Parra-Rapado L., Planchenault D., Weber V. J. Org. Chem. 62:1997;1630-1641.
47. Eaborn C., Bott R.W. MacDiarmid A.G. Organometallic Compounds of the IV Elements. Vol. 1 (Part 1):1968;Marcel Dekker, New York.
48. Tanaka K., Uneme H., Matsui S. Chem. Lett. 1980;287-288.
49. Kramer G.W., Brown H.C. J. Org. Chem. 42:1977;2292-2299.
50. Julia M., Mansuy D. Bull. Soc. Chim. Fr. 1972;2684-2689.
51. Medlik-Balan A., Klein J. Tetrahedron. 36:1980;299-304.
52. Truce W.E., Hollister K.R., Lindy L.B., Parr J.E. J. Org. Chem. 33:1968;43-47.
53. Angelaud R., Landais Y., Schenk K. Tetrahedron Lett. 38:1997;1407-1411.
54. Aldrich No. 42,462-5.