Novel aspects of the ferrier carbocyclic ring-transformation reaction

Pál László, István F. Pelyvás, Ferenc Sztaricskai, László Szilágyi, Árpád Somogyi

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The mercury salt-mediated carbocyclic ring-transformation reaction of the 3-azido (4), 3-benzamido (8), and 3-trifluoroacetamido (11) derivatives of methyl 4-O-benzoyl-2,3,6-trideoxy-β-d-erythro-hex-5-enopyranoside, methyl 3-azido-4-O-benzoyl-2,3,6-trideoxy-α-d-threo-hex-5-enopyranoside (16), and its 3-O-benzoyl-β- (14) and 3-deoxy-α (18) analogues has been investigated. The resulting cyclohexanone derivatives 20-23, together with all of the "Ferrier-ketones", have the newly generated HO-5 and the 3-substituent trans. The role of the mercury atom in exerting stereocontrol has been substantiated through the formation of the C-5 diastereoisomeric cyclohexanones 24a and 24b in the Ferrier-reaction of 18, which has no 3-substituent.

Original languageEnglish
Pages (from-to)227-239
Number of pages13
JournalCarbohydrate Research
Volume175
Issue number2
DOIs
Publication statusPublished - May 15 1988

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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