Synthesis of 3-chloro-Δ3-cephem-4-carboxylate by addition/cyclization of allenecarboxylate. Copper(II)-promoted aerobic oxidation of arenesulfinic acids

Hideo Tanaka, Ryo Kikuchi, Sigeru Torii

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The selective transformation of allenecarboxylate derived from penicillin into 3-chloro-Δ3-cephem-4-carboxylate was successfully achieved by an addition/cyclization reaction with chloride salts in aerobic media containing a copper(II) catalyst, in which copper(II)-catalyzed aerobic oxidation of in situ generated benzenesulfinate ion into less nucleophilic sulfonate ion prior to the nucleophilic addition of the former ion to the allenecarboxylate would completely eliminate the formation of undesired 3-phenylsulfonyl-Δ3-cephem-4-carboxylate. Under similar aerobic conditions, arenesulfinates salts and arenesulfinic acids were smoothly oxidized to the corresponding sulfonate salts and sulfonic acids, respectively.

Original languageEnglish
Pages (from-to)1391-1396
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume69
Issue number5
DOIs
Publication statusPublished - May 1996

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Cyclization
Copper
Salts
Ions
Oxidation
Acids
Sulfonic Acids
Penicillins
Chlorides
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of 3-chloro-Δ3-cephem-4-carboxylate by addition/cyclization of allenecarboxylate. Copper(II)-promoted aerobic oxidation of arenesulfinic acids. / Tanaka, Hideo; Kikuchi, Ryo; Torii, Sigeru.

In: Bulletin of the Chemical Society of Japan, Vol. 69, No. 5, 05.1996, p. 1391-1396.

Research output: Contribution to journalArticle

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