Palladium-catalyzed annelation onto N, N-dialkylanilines by tetrahydrofuran. Stereospecific formation of heterotricyclic compounds via cation-radical intermediates

T Sakakibara, S Karasumaru…

Index: Sakakibara,T.; Karasumara,S.; Kawano,I. Journal of the American Chemical Society, 1985 , vol. 107, p. 6417

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Citation Number: 11

Abstract

(10 mmd 1 50'c/83 hr compound 3b7 shows no carbonyl absorption in its IR and a doublet (J= 4.0 Hz, 1H) at 6 4.53 in its HI NMR. The doublet signal assigned to the C-9a proton of 3b was decoupled to a singlet by irradiating multiplet signals near 6 2.4, which may be assigned to a proton on C-4a. The small coupling constant (J4a-9a= 4.0 Hz) may be attributed to the existence of cis-fused tetrahydropyran ring8