Stereoselective intermolecular carboazidation of chiral allylsilanes

Organic Letters

Volumn 4, Issue 24, 2002, Pages 4257-4260

  Chabaud, Laurent ^a   Landais, Yannick ^a   Renaud, Philippe ^b  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0012667696     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026824y     Document Type: Article

References (33)

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3. For a general review on radical reactions, see: Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds; Wiley-VCH: Weinheim, 2001; Vols. 1 and 2. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1988. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, 1991; Vol. 4, p 715. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Synthesis; Wiley: Chichester, 1995. Chatgilialoglu, C.; Renaud, P. In General Aspects of the Chemistry of Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, 1999; p 501.
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5. For a general review on radical reactions, see: Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds; Wiley-VCH: Weinheim, 2001; Vols. 1 and 2. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1988. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, 1991; Vol. 4, p 715. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Synthesis; Wiley: Chichester, 1995. Chatgilialoglu, C.; Renaud, P. In General Aspects of the Chemistry of Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, 1999; p 501.
6. For a general review on radical reactions, see: Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds; Wiley-VCH: Weinheim, 2001; Vols. 1 and 2. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1988. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, 1991; Vol. 4, p 715. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Synthesis; Wiley: Chichester, 1995. Chatgilialoglu, C.; Renaud, P. In General Aspects of the Chemistry of Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, 1999; p 501.
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13. The silyl aroup is expected to stabilize polarized transition states bearing a partially positive charge in β-position. Therefore, transition state conformations allowing such a stabilization should be favored. See rets 20 and 21.
14. Diasteroselective azidation of β-silyl Barton ester are reported by Masterson and Porter in the preceding paper: Porter, N. A.; Masterson, D. S. Org. Lett. 2002, 4, 4253-4256.
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18. Schaumann, E.; Kirschning, A. Tetrahedron Lett. 1988, 29, 4281.
19. The relative stereochemistry of 6 and 7 was assigned by analogy to the reaction with propylene oxide where product stereochemistry was proven by X-ray crystallography (results to be published).
20. 2 (0.27 mL, 0.52 mmol), and di-tert-butylhyponitrite (2.5 mg, 0.015 mmol) in benzene (1.5 mL) was heated under reflux. The reaction was monitored by TLC and further portions of di-tert-butylhyponitrite (2.5 mg, 0.015 mmol) were added every 1.5 h. Upon completion, the solvent was removed under reduced pressure, the crude product was filtered through silica gel (hexane, then hexane/EtOAc 9:1), and the combined fractions were concentrated in vacuo. The residue was purified by chromatography (hexane/EtOAc).
21. Arimoto, M.; Yamaguchi, H.; Fujita, E.; Nagao, Y.; Ochiai, M. Chem. Pharm. Bull. 1989, 37, 12, 3221. Bernhard, W.; Fleming, I. J. Organomet. Chem. 1984, 271, 281.
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23. The coupling constant J = 9 Hz between the two vicinal olefinic protons and NOESY experiments allowed us to assign unambiguously the (Z)-stereochemistry for the double bond of 15 and 16.
24. A detailed study of the stereospecificity of this elimination is currently underway in Bordeaux. Chabaud, L.; Landais, Y. Unpublished results.
25. The stereochemical outcome of radical addition to branched allylsilane was rationalized by a Felkin-Anh transition state (ref 7).
26. Thoma, G.; Curran, D. P.; Geib, S.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585.
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28. Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. 1989, 37, 57. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
29. 3 group is known to be stabilized by ∼3 kcal/ mol: Auner, N.; Walsh, R.; Westrup, J. J. Chem. Soc., Chem. Commun. 1986, 207.
30. For a related example, see: Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 38, 233.
31. Fleming, I. Chemtracts: Org. Chem. 1996, 9, 1. Landais, Y.; Jones, G. Tetrahedron 1996, 52, 7599.
32. Fleming, I. Chemtracts: Org. Chem. 1996, 9, 1. Landais, Y.; Jones, G. Tetrahedron 1996, 52, 7599.
33. Tamao, K. In Advances in Silicon Chemistry; Jai Press Inc.: Greenwich, CT 1996; Vol. 3, p 1.