TY - JOUR
T1 - Synthesis of dihydropyrroles by the intramolecular addition of alkylideneaminyl radicals generated from O-2,4-dinitrophenyloximes of γ,δ- unsaturated ketones
AU - Uchiyama, Katsuya
AU - Hayashi, Yujiro
AU - Narasaka, Koichi
PY - 1999/7/16
Y1 - 1999/7/16
N2 - Alkylideneaminyl radicals are generated from O-2,4-dinitrophenyloximes of γ,δ-unsaturated ketones by treatment with NaH and 3,4- methylenedioxyphenol. The resulting radical species successively add to the olefinic moiety intramolecularly to afford dihydropyrroles in the presence of a radical trapping agent. This method is applied for the stereoselective synthesis of xenovenine, a bicyclic 3,5-dialkylpyrrolizidine alkaloid.
AB - Alkylideneaminyl radicals are generated from O-2,4-dinitrophenyloximes of γ,δ-unsaturated ketones by treatment with NaH and 3,4- methylenedioxyphenol. The resulting radical species successively add to the olefinic moiety intramolecularly to afford dihydropyrroles in the presence of a radical trapping agent. This method is applied for the stereoselective synthesis of xenovenine, a bicyclic 3,5-dialkylpyrrolizidine alkaloid.
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U2 - 10.1016/S0040-4020(99)00453-6
DO - 10.1016/S0040-4020(99)00453-6
M3 - Article
AN - SCOPUS:0033575448
SN - 0040-4020
VL - 55
SP - 8915
EP - 8930
JO - Tetrahedron
JF - Tetrahedron
IS - 29
ER -