Using a Temporary Silicon Connection in Stereoselective Allylation with Allylsilanes: Application to the Synthesis of Stereodefined 1,2,4-Triols

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4231-4234

  Beignet, Julien ^a   Cox, Liam R ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; SILANE DERIVATIVE; SILICON;

ALLYLATION; ARTICLE; MOLECULAR DYNAMICS; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344514091     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035762o     Document Type: Article

References (29)

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9. Silacyclobutane systems would be an important exception: (a) Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. J. Am. Chem. Soc. 1994, 116, 7026-7043. (b) Myers, A. G.; Kephart, S. E.; Chen, H. J. Am. Chem. Soc. 1992, 114, 7922-7923.
10. For an enantioselective allylation reaction employing allyltrialkylsilanes: Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363-2365.
11. For some very recent examples: (a) Denmark, S. E.; Fu, J. Chem. Commun. 2003, 167-170. (b) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946-948. (c) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537.
12. For some very recent examples: (a) Denmark, S. E.; Fu, J. Chem. Commun. 2003, 167-170. (b) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946-948. (c) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537.
13. For some very recent examples: (a) Denmark, S. E.; Fu, J. Chem. Commun. 2003, 167-170. (b) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946-948. (c) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537.
14. Cox, L. R.; Ley, S. V. in Templated Organic Synthesis; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 10, pp 275-395 and references therein.
15. 4 as a Lewis acid was important here for ensuring an intramolecular allylation. A T. S. in which the Ti Lewis acid coordinates to both the aldehyde and silyl ether oxygen was invoked for rationalizing the stereochemical outcome of the reaction.
16. Reetz, M. T.; Jung, A. J. Am. Chem. Soc. 1983, 105, 4833-4835.
17. See for example: (a) Hioki, H.; Okuda, M.; Miyagi, W.; Itô, S. Tetrahedron Lett. 1993, 34, 6131-6134. (b) Martin, O. R.; Rao, S. P.; Kurz, K. G.; El-Shenawy, H. A. J. Am. Chem. Soc. 1988, 110, 8698-8700.
18. See for example: (a) Hioki, H.; Okuda, M.; Miyagi, W.; Itô, S. Tetrahedron Lett. 1993, 34, 6131-6134. (b) Martin, O. R.; Rao, S. P.; Kurz, K. G.; El-Shenawy, H. A. J. Am. Chem. Soc. 1988, 110, 8698-8700.
19. Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007.
20. 2, TfOH.
21. Diene 5 may be formed in a variety of ways. We currently favor a mechanism involving a vinylogous silicon-mediated olefination as this best accounts for the excellent (E)-stereoselectivity observed. (a) Stragies, R.; Blechert, S. Tetrahedron 1999, 55, 8179-8188. (b) Bradley, G. W.; Thomas, E. J. Synlett 1997, 629-631. (c) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1984, 534-536.
22. Diene 5 may be formed in a variety of ways. We currently favor a mechanism involving a vinylogous silicon-mediated olefination as this best accounts for the excellent (E)-stereoselectivity observed. (a) Stragies, R.; Blechert, S. Tetrahedron 1999, 55, 8179-8188. (b) Bradley, G. W.; Thomas, E. J. Synlett 1997, 629-631. (c) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1984, 534-536.
23. Diene 5 may be formed in a variety of ways. We currently favor a mechanism involving a vinylogous silicon-mediated olefination as this best accounts for the excellent (E)-stereoselectivity observed. (a) Stragies, R.; Blechert, S. Tetrahedron 1999, 55, 8179-8188. (b) Bradley, G. W.; Thomas, E. J. Synlett 1997, 629-631. (c) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1984, 534-536.
24. 2.
25. For a detailed review on this reaction: Fleming, I. Chemtracts: Org. Chem. 1996, 9, 1-64.
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27. For elucidating the 1,3-relative stereochemistry: Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515; and the 1,2-relative stereochemistry: Dana, G.; Danechpajouh, H. Bull. Soc. Chim. Fr. 1980, 2, 395-399.
28. For elucidating the 1,3-relative stereochemistry: Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515; and the 1,2-relative stereochemistry: Dana, G.; Danechpajouh, H. Bull. Soc. Chim. Fr. 1980, 2, 395-399.
29. Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223.