Convenient Radical. ALPHA.-Monoallylations of Carbonyl Compounds.

Y Watanabe, T Yoneda, T Okumura, Y Ueno…

Index: Watanabe, Yoshihiko; Yoneda, Tetsuo; Okumura, Tatsuya; Ueno, Yoshio; Toru, Takeshi Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 10 p. 3030 - 3033

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Citation Number: 10

Abstract

Free radical allylations of α-seleno carbonyl compounds with tributyl-substituted 2, 4- pentadienyltin, 2-methyl-2-propenyltin, 2-butenyltin, and 3-methyl-2-butenyltin, are described. Such successful C–C bond formations, in particular with the 2-butenyltin and the 3-methyl-2-butenyltin, are owing to the high reactivity of the α-carbon radical, generated from α-seleno carbonyl compounds, toward allylic tin compounds.

~64%

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Lewis Acid Alkylation of Ketones Using SN1-reactive Acetates

[Reetz, M. T.; Huettenhain, S.; Huebner, F. Synthetic Communications, 1981 , vol. 11, # 3 p. 217 - 222]

Synthesis of prenylated indoles

[Wenkert, Ernest; Angell, E. Charles; Ferreira, Vitor F.; Michelotti, Enrique L.; Piettre, Serge R.; et al. Journal of Organic Chemistry, 1986 , vol. 51, # 12 p. 2343 - 2351]