TY - JOUR
T1 - Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group
AU - Ohno, Hiroaki
AU - Mimura, Norio
AU - Otaka, Akira
AU - Tamamura, Hirokazu
AU - Fujii, Nobutaka
AU - Ibuka, Toshiro
AU - Shimizu, Isao
AU - Satake, Akiharu
AU - Yamamoto, Yoshinori
PY - 1997/9/22
Y1 - 1997/9/22
N2 - The palladium-catalyzed reduction of various N-arenesulfonylaziridines bearing α,β-unsaturated ester groups with formic acid and the stereochemistry of the reaction products have been investigated in detail. In all cases examined, (Z)-α,β-enoates, (E)-α,β-enoates, and (E)-β,γ-enoates bearing amino functionality at the δ-position were obtained. The formation of these three reduction products was taken as an indication that palladium-catalyzed isomerization occurs prior to the reduction step.
AB - The palladium-catalyzed reduction of various N-arenesulfonylaziridines bearing α,β-unsaturated ester groups with formic acid and the stereochemistry of the reaction products have been investigated in detail. In all cases examined, (Z)-α,β-enoates, (E)-α,β-enoates, and (E)-β,γ-enoates bearing amino functionality at the δ-position were obtained. The formation of these three reduction products was taken as an indication that palladium-catalyzed isomerization occurs prior to the reduction step.
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U2 - 10.1016/S0040-4020(97)00817-X
DO - 10.1016/S0040-4020(97)00817-X
M3 - Article
AN - SCOPUS:0030767529
SN - 0040-4020
VL - 53
SP - 12933
EP - 12946
JO - Tetrahedron
JF - Tetrahedron
IS - 38
ER -