Stereoselective phenyl migration from silicon to carbon

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8829-8832

  Studer, Armido ^a   Bossart, Martin ^a   Steen, Hanno ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; SILANE DERIVATIVE; SILICON; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032569916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02045-0     Document Type: Article

References (36)

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15. c) M. L. E. N. da Mata, W. B. Motherwell, F. Ujjainwalla, ibid. 1997, 38, 141; E. Bonfand, W. B. Motherwell, A. M. K. Pennell, M. K. Uddin, F. Ujjainwalla, Heterocycles, 1997, 46, 523.
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18. [7] J. W. Wilt, C. F. Dockus, J. Am. Chem. Soc. 1970, 92, 5813; J. W. Wilt, W. K. Chwang, ibid. 1974, 96, 6194; J. W. Wilt, W. K. Chwang, C. F. Dockus, N. M. Tomiuk, ibid. 1978, 100, 5534.
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21. [9] For diastereoselective radical phenyl migrations from sulfur to carbon see: H. J. Köhler, W. N. Speckamp, J. Chem. Soc. Chem. Commun. 1980, 142; D. L. Clive, T. L. B. Boivin, J. Org. Chem. 1989, 54, 1997; P. C. Montevecchi, M. L. Navacchia, J. Org. Chem. 1998, 63, 537; A. Studer, M. Bossart, J. Chem. Soc., Chem. Commun, in press. See also: J. Aubé, X. Peng, Y. Wang, F. Takusagawa, J. Am. Chem. Soc. 1992, 114, 5466;
22. [9] For diastereoselective radical phenyl migrations from sulfur to carbon see: H. J. Köhler, W. N. Speckamp, J. Chem. Soc. Chem. Commun. 1980, 142; D. L. Clive, T. L. B. Boivin, J. Org. Chem. 1989, 54, 1997; P. C. Montevecchi, M. L. Navacchia, J. Org. Chem. 1998, 63, 537; A. Studer, M. Bossart, J. Chem. Soc., Chem. Commun, in press. See also: J. Aubé, X. Peng, Y. Wang, F. Takusagawa, J. Am. Chem. Soc. 1992, 114, 5466;
23. [9] For diastereoselective radical phenyl migrations from sulfur to carbon see: H. J. Köhler, W. N. Speckamp, J. Chem. Soc. Chem. Commun. 1980, 142; D. L. Clive, T. L. B. Boivin, J. Org. Chem. 1989, 54, 1997; P. C. Montevecchi, M. L. Navacchia, J. Org. Chem. 1998, 63, 537; A. Studer, M. Bossart, J. Chem. Soc., Chem. Commun, in press. See also: J. Aubé, X. Peng, Y. Wang, F. Takusagawa, J. Am. Chem. Soc. 1992, 114, 5466;
24. [9] For diastereoselective radical phenyl migrations from sulfur to carbon see: H. J. Köhler, W. N. Speckamp, J. Chem. Soc. Chem. Commun. 1980, 142; D. L. Clive, T. L. B. Boivin, J. Org. Chem. 1989, 54, 1997; P. C. Montevecchi, M. L. Navacchia, J. Org. Chem. 1998, 63, 537; A. Studer, M. Bossart, J. Chem. Soc., Chem. Commun, in press. See also: J. Aubé, X. Peng, Y. Wang, F. Takusagawa, J. Am. Chem. Soc. 1992, 114, 5466;
25. [9] For diastereoselective radical phenyl migrations from sulfur to carbon see: H. J. Köhler, W. N. Speckamp, J. Chem. Soc. Chem. Commun. 1980, 142; D. L. Clive, T. L. B. Boivin, J. Org. Chem. 1989, 54, 1997; P. C. Montevecchi, M. L. Navacchia, J. Org. Chem. 1998, 63, 537; A. Studer, M. Bossart, J. Chem. Soc., Chem. Commun, in press. See also: J. Aubé, X. Peng, Y. Wang, F. Takusagawa, J. Am. Chem. Soc. 1992, 114, 5466;
26. [10] A. Studer, Angew. Chem. 1998, 110, 507; Angew. Chem. Int. Ed. 1998, 37, 462.
27. [10] A. Studer, Angew. Chem. 1998, 110, 507; Angew. Chem. Int. Ed. 1998, 37, 462.
28. [12] The germylated and silylated chlorosilanes were prepared analogously. Triphenyl-and t-butyldiphenylsilyl chloride (TBDPSCl) are commercially available. The TBDPS ether 4 was prepared in DMF using imidazole as base. In the formation of 1 partial epimerization (30%) occurred during silylation. All the compounds described in the present communication were prepared as racemic mixtures. In the equations only one enantiomer is shown.
29. [12] A. Kawachi, N. Doi, K. Tamao, J. Am. Chem. Soc. 1997, 119, 233.
30. [14] as a colorless oil: 28 mg (70%).
31. [14] The relative configuration of 7 has previously been assigned: J. M. Brown, R. G. Naik, J. Chem. Soc. Chem. Commun. 1982, 348. As an additional side product 1-methylbutanol (not quantified due to its volatility) was formed. 1-Methylbutanol is derived from the direct reduction product. In all the other systems investigated (entries 2-6) the reduction product was also observed.
32. [15] A. Studer, H. Steen, Chem. Eur. J., accepted for publication.
33. [16] The relative configuration of the major isomer was assigned after oxidation (Swern) to the corresponding known aldehyde: I. Fleming, J. J. Lewis, J. Chem. Soc. Perkin Trans 1 1992, 3257.
34. [17] Spirocyclic cyclohexadienyl radicals with two silyl substituents at the spiro position have been characterized by EPR spectroscopy. A 6-membered chair conformation was suggested for the non spin carrying ring: H. Sakurai, I. Nozue, A. Hosomi, J. Am. Chem. Soc. 1976, 98, 8279.
35. [18] D. P. Curran, M-H. Chen, D. Kim, J. Am. Chem. Soc. 1989, 111, 6265.
36. [19] The relative configuration was assigned by analogy.