Palladium-catalyzed reactions of alkenyloxiranes with carbon monoxide

Isao Shimizu, Takashi Maruyama, Toshiyuki Makuta, Akio Yamamoto

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Reaction of alkenyloxiranes with carbon monoxide in the presence of palladium catalyst gives unsaturated esters, β-lactones, dienes, and allylic alcohols. The selectivity of the reaction depends on the nature of the alkenyloxiranes. Carbonylation pruducts were obtained in the reaction of terminal alkenyloxiranes and alkenyloxirans having electron-donating substituent, whereas carbonylation scarcely took place in the reaction of alkenyloxiranes having electron-withdrawing groups; dienes and allylic alcohols were produced instead of carbonylation products.

Original languageEnglish
Pages (from-to)2135-2138
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number13
DOIs
Publication statusPublished - 1993 Mar 26

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Carbonylation
Palladium
Carbon Monoxide
Electrons
Lactones
Esters
Catalysts
allyl alcohol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalyzed reactions of alkenyloxiranes with carbon monoxide. / Shimizu, Isao; Maruyama, Takashi; Makuta, Toshiyuki; Yamamoto, Akio.

In: Tetrahedron Letters, Vol. 34, No. 13, 26.03.1993, p. 2135-2138.

Research output: Contribution to journalArticle

Shimizu, I, Maruyama, T, Makuta, T & Yamamoto, A 1993, 'Palladium-catalyzed reactions of alkenyloxiranes with carbon monoxide', Tetrahedron Letters, vol. 34, no. 13, pp. 2135-2138. https://doi.org/10.1016/S0040-4039(00)60364-7
Shimizu, Isao ; Maruyama, Takashi ; Makuta, Toshiyuki ; Yamamoto, Akio. / Palladium-catalyzed reactions of alkenyloxiranes with carbon monoxide. In: Tetrahedron Letters. 1993 ; Vol. 34, No. 13. pp. 2135-2138.
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