Cycloadditions of allylsilanes, part 11. Stereoselective synthesis of hydroxycyclopentanes and hydroxymethylcyclobutanes by titanium tetrachloride-promoted [3+2] and [2+2] cycloadditions of sterically hindered allylsilanes and subsequent oxidative cleavage of the carbon-silicon bond

Synlett

Volumn , Issue 6, 1998, Pages 613-616

  Knölker, Hans Joachim ^a   Jones, Peter G ^b   Wanzl, Günter ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001233724     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1727     Document Type: Article

References (46)

1. H. Sakurai, Pure Appl. Chem. 1982, 54, 1;
2. A. Hosomi, Acc. Chem. Res. 1988, 21, 200;
3. I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57;
4. C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293;
5. E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375;
6. I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
7. A. Hosorni, H. Sakurai, J. Am. Chem. Soc. 1977, 99, 1673;
8. T. A. Blumenkopf, C. H. Heathcock, J. Am. Chem. Soc. 1983, 105, 2354;
9. D. Schinzer, Synthesis 1988, 263;
10. G. Majetich in Organic Synthesis, Theory and Applications, Vol. 1 (Ed.: T. Hudlicky), JAI Press, Greenwich (CT), 1989, p. 173.
11. a) H.-J. Knölker, P. G. Jones, J.-B. Pannek, Synlett 1990, 429;
12. b) H.-J. Knölker, P. G. Jones, J.-B. Pannek, A. Weinkauf, Synlett 1991, 147;
13. c) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 1993, 105, 1104;
14. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081;
15. d) H.-J. Knölker, R. Graf, Tetrahedron Lett. 1993, 34, 4765;
16. e) H.-J. Knölker, N. Foitzik, R. Graf, J.-B. Pannek, P. G. Jones, Tetrahedron 1993, 49, 9955;
17. f) H.-J. Knölker, R. Graf, Synlett 1994, 131;
18. g) H.-J. Knölker, R. Graf, Synlett 1996, 1155.
19. H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538.
20. R. L. Danheiser, B. R. Dixon, R. W. Gleason, J. Org. Chem. 1992, 57, 6094;
21. R. L. Danheiser, T. Takahashi, B. Bertok, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845;
22. J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345;
23. M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073;
24. G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158.
25. For a review on the cycloadditions of allyltriisopropylsilane, see: Part 10. H.-J. Knölker, J. Prakt. Chem. 1997, 339, 304.
26. H.-J. Knölker, G. Baum, R. Graf, Angew. Chem. 1994, 106, 1705;
27. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612.
28. M. Hojo, K. Tomita, Y. Hirohara, A. Hosomi, Tetrahedron Lett. 1993, 34, 8123;
29. H. Monti, G. Audran, J.-P. Monti, G. Léandri, Synlett 1994, 403;
30. G. P. Brengel, C. Rithner, A. I. Meyers, J. Org. Chem. 1994, 59, 5144.
31. I. Fleming, R. Henning, H. Flaut, J. Chem. Soc., Chem. Commun. 1984, 29;
32. K. Tamao, T. Kakui, M. Akita, T. Iwahara, R. Kanatani, J. Yoshida, M. Kumada, Tetrahedron 1983, 39, 983;
33. K. Tamao, N. Ishida, T. Tanaka, M. Kumada, Organometallics 1983, 2, 1694;
34. I. Fleming, R. Henning, D. C. Parker, H. E. Plaut, P. E. J. Sanderson, J. Chem. Soc. Perkin Trans. 1 1995, 317.
35. For recent reviews, see: I. Fleming, Chemtracts-Organic Chemistry 1996, 9, 1;
36. G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599;
37. K. Tamao in Advances in Silicon Chemistry, Vol. 3, JAI Press, Greenwich (CT), 1996, p. 1; et loc. cit.
38. a) H.-J. Knölker, G. Wanzl, Synlett 1995, 378;
39. b) for the same transformation with dimethyltritylsilylcyclopentanes, see: G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230.
40. H. Rupe, E. Kambli, Helv. Chim. Acta 1926, 9, 672;
41. O. F. Beumel, Jr., R. F. Harris, J. Org. Chem. 1964, 29, 1872;
42. C. M. Marson, A. J. Walker, J. Pickering, S. Harper, R. Wrigglesworth, S. J. Edge, Tetrahedron 1993, 49, 10317.
43. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101176. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223336-033; e-mail: deposit@ccdc.cam.ac.uk).
44. E. Winter, R. Brückner, Synlett 1994, 1049;
45. K. Behrens, B. O. Kneisel, M. Noltemeyer, R. Brückner, Liebigs Ann. Chem. 1995, 385.
46. F. Le Bideau, C. Aubert, M. Malacria, Tetrahedron: Asymmetry 1995, 6, 697.