Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group

Hiroaki Ohno, Norio Mimura, Akira Otaka, Hirokazu Tamamura, Nobutaka Fujii, Toshiro Ibuka, Isao Shimizu, Akiharu Satake, Yoshinori Yamamoto

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17 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)12933-12946
Number of pages14
JournalTetrahedron
Volume53
Issue number38
DOIs
Publication statusPublished - 1997 Sep 22

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Ohno, H., Mimura, N., Otaka, A., Tamamura, H., Fujii, N., Ibuka, T., Shimizu, I., Satake, A., & Yamamoto, Y. (1997). Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group. Tetrahedron, 53(38), 12933-12946. https://doi.org/10.1016/S0040-4020(97)00817-X