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

Research output: Contribution to journalArticle

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

Fingerprint

formic acid
Bearings (structural)
Aziridines
Palladium
Esters
Stereochemistry
Isomerization
Reaction products

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Ohno, H., Mimura, N., Otaka, A., Tamamura, H., Fujii, N., Ibuka, T., ... 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

Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group. / Ohno, Hiroaki; Mimura, Norio; Otaka, Akira; Tamamura, Hirokazu; Fujii, Nobutaka; Ibuka, Toshiro; Shimizu, Isao; Satake, Akiharu; Yamamoto, Yoshinori.

In: Tetrahedron, Vol. 53, No. 38, 22.09.1997, p. 12933-12946.

Research output: Contribution to journalArticle

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, vol. 53, no. 38, pp. 12933-12946. https://doi.org/10.1016/S0040-4020(97)00817-X
Ohno, Hiroaki ; Mimura, Norio ; Otaka, Akira ; Tamamura, Hirokazu ; Fujii, Nobutaka ; Ibuka, Toshiro ; Shimizu, Isao ; Satake, Akiharu ; Yamamoto, Yoshinori. / Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group. In: Tetrahedron. 1997 ; Vol. 53, No. 38. pp. 12933-12946.
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