Vinyl radical cyclization onto imino group. Selective 6-endo cyclization onto aldimines leading to 3-methylenepiperidines

Tetrahedron Letters

Volumn 40, Issue 8, 1999, Pages 1515-1518

  Ryu, Ilhyong ^a   Ogura, Shin ichi ^a   Minakata, Satoshi ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; RADICAL; TIN; VINYL DERIVATIVE;

ARTICLE; CYCLIZATION;

EID: 0033582589     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02666-5     Document Type: Article

References (12)

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4. For the mechanistic aspects of -exo/6-endo acyl radical cyclization onto C=C, see: (a) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komȧtsu, M. Synlett 1997, 1265-1268.
5. (b) Chatgilialoglu, C.; Ferreri, C.; Lucarini, M.; Venturini, A.; Zavitsas, A. A. Chem. Eur. J. 1997, 3, 376-387.
6. For alkyl radical cyclizations onto imino group, see: Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron 1995, 51, 7959-7980.
7. Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838-5839.
8. 17N requires 139.1361).
9. -1 at °C). (a) Tomaszewski, M. J.; Warkentin, J. Tetrahedron Lett. 1992, 33, 2123-2126.
10. (b) Tomaszewski, M. J.; Warkentin, J.; Werstiuk, N. H. Aust. J. Chem. 1995, 48, 291-321.
11. For some other examples of aryl radical cyclizations, see: (c) Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Chem. Lett. 1990, 315-316.
12. (d) Takano, S.; Suzuki, M.; Ogasawara, K. Heterocycles 1994, 37, 149-152.