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Volumn 62, Issue 20, 1997, Pages 7028-7032

Radical Allylations with Trimethyl[2-[(tributylstannyl)methyl]-2-propenyl]silane or Trimethyl[2-[(triphenylstannyl)-methyl] -2-propenyl] silane

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EID: 0000733289     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9705529     Document Type: Article
Times cited : (40)

References (66)
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    • Intermolecular allylation can be done directly, or after other radical reactions, such as cyclization, carbonylation, intermolecular radical addition, etc.: e.g., (a) see ref 1c. (b) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288. (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029. (d) Ryu, I.; Yamazaid, H.; Kusano, K; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 8558. (e) Ryu, I.; Yamazaki, H.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 1187. (f) Tamao, K.; Nagata, K.; Ito, Y.; Maeda, K.; Shiro, M. Synlett 1994, 257. (g) Moriya, O.; Kakihana, M.; Urata, Y.; Sugizaki, T.; Kageyama, T.; Ueno, Y.; Endo, T. J. Chem. Soc., Chem. Commun. 1985, 1401. (h) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (i) Keck, G. E.; Kordik, C. P. Tetrahedron Lett. 1993, 34, 6875.
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    • Intermolecular allylation can be done directly, or after other radical reactions, such as cyclization, carbonylation, intermolecular radical addition, etc.: e.g., (a) see ref 1c. (b) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288. (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029. (d) Ryu, I.; Yamazaid, H.; Kusano, K; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 8558. (e) Ryu, I.; Yamazaki, H.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 1187. (f) Tamao, K.; Nagata, K.; Ito, Y.; Maeda, K.; Shiro, M. Synlett 1994, 257. (g) Moriya, O.; Kakihana, M.; Urata, Y.; Sugizaki, T.; Kageyama, T.; Ueno, Y.; Endo, T. J. Chem. Soc., Chem. Commun. 1985, 1401. (h) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (i) Keck, G. E.; Kordik, C. P. Tetrahedron Lett. 1993, 34, 6875.
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    • Intermolecular allylation can be done directly, or after other radical reactions, such as cyclization, carbonylation, intermolecular radical addition, etc.: e.g., (a) see ref 1c. (b) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288. (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029. (d) Ryu, I.; Yamazaid, H.; Kusano, K; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 8558. (e) Ryu, I.; Yamazaki, H.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 1187. (f) Tamao, K.; Nagata, K.; Ito, Y.; Maeda, K.; Shiro, M. Synlett 1994, 257. (g) Moriya, O.; Kakihana, M.; Urata, Y.; Sugizaki, T.; Kageyama, T.; Ueno, Y.; Endo, T. J. Chem. Soc., Chem. Commun. 1985, 1401. (h) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (i) Keck, G. E.; Kordik, C. P. Tetrahedron Lett. 1993, 34, 6875.
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    • But compare the following: (b) Easton, C. J.; Scharfbillig, T. M. J. Org. Chem. 1990, 55, 384. (c) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron 1995, 51, 4183.
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    • Usually, R = Bu. For R = Ph, see refs 1c, 4f, 5a, 5b, 6b; for R = Me, see refs 1f, 1i, 6b
    • Usually, R = Bu. For R = Ph, see refs 1c, 4f, 5a, 5b, 6b; for R = Me, see refs 1f, 1i, 6b.
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    • For an exception, see ref 8a
    • For an exception, see ref 8a.
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    • 3), see refs 1g, 6b, 6c.
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    • Reagent 4a is not stable to silica chromatography (cf. ref 19b)
    • Reagent 4a is not stable to silica chromatography (cf. ref 19b).


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