Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion

Akiharu Satake, Hideo Ishii, Isao Shimizu, Yoichi Inoue, Hajime Hasegawa, Akio Yamamoto

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Ring opening reactions of 1-acetyl-4-vinyl-2-azetidinones in the presence of palladium(0)-n-Bu3P catalyst gave 2,4-pentadienamides in good yields, whereas 2-substituted-1,3-dienes were produced by the reaction of 1-sulfonyl-2-vinyl-2-methylazetidines. Ring opening dimerization took place to give 1,7-ditrifluoromethanesulfonyl-1,7-diazacyclododecane in the reaction of 1-trifluoromethanesulfonyl-2-vinylazetidine.

Original languageEnglish
Pages (from-to)5331-5340
Number of pages10
JournalTetrahedron
Volume51
Issue number18
DOIs
Publication statusPublished - 1995 May 1

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Dimerization
Palladium
Amides
Anions
Catalysts
2-azetidinone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion. / Satake, Akiharu; Ishii, Hideo; Shimizu, Isao; Inoue, Yoichi; Hasegawa, Hajime; Yamamoto, Akio.

In: Tetrahedron, Vol. 51, No. 18, 01.05.1995, p. 5331-5340.

Research output: Contribution to journalArticle

Satake, Akiharu ; Ishii, Hideo ; Shimizu, Isao ; Inoue, Yoichi ; Hasegawa, Hajime ; Yamamoto, Akio. / Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion. In: Tetrahedron. 1995 ; Vol. 51, No. 18. pp. 5331-5340.
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