Highly stereo- and regioselective formation of 2-oxazolone telomers, potential synthetic intermediates for amino sugars

Takehisa Kunieda, Yoshihiro Abe, Yoichi Iitaka, Masaaki Hirobe

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Free radical initiated reaction of 3-acyl-2-oxazolones proceeds smoothly in polyhalomethanes, which function as telogens, to give type 3 telomers of synthetic potential with high regio- and stereoselectivity, while the 3-alkyl derivatives failed to give such polyfunctional products. This particular telomerization can be controlled exclusively in the tram "head-to-tail" addition mode, as elucidated by 1H and 13C NMR and X-ray analysis of the products. Thus, the 3-benzoyl heterocycle 7 gave trans-4-chloro-5-(trichloromethyl)-2-oxazolidone (8) as a sole 1:1 adduct and two trans isomere of 4′-chloro-5-(trichloromethyl)[4,5′-bioxazolidinyl]-2,2′-dione (9a,b) as 2:1 telomers. Some characteristic reactions of the telomers are described.

Original languageEnglish
Pages (from-to)4291-4297
Number of pages7
JournalJournal of Organic Chemistry
Volume47
Issue number22
Publication statusPublished - 1982
Externally publishedYes

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Free radical reactions
Oxazolone
Oxazolidinones
Amino Sugars
Stereoselectivity
Regioselectivity
X ray analysis
Nuclear magnetic resonance
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Highly stereo- and regioselective formation of 2-oxazolone telomers, potential synthetic intermediates for amino sugars. / Kunieda, Takehisa; Abe, Yoshihiro; Iitaka, Yoichi; Hirobe, Masaaki.

In: Journal of Organic Chemistry, Vol. 47, No. 22, 1982, p. 4291-4297.

Research output: Contribution to journalArticle

Kunieda, Takehisa ; Abe, Yoshihiro ; Iitaka, Yoichi ; Hirobe, Masaaki. / Highly stereo- and regioselective formation of 2-oxazolone telomers, potential synthetic intermediates for amino sugars. In: Journal of Organic Chemistry. 1982 ; Vol. 47, No. 22. pp. 4291-4297.
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