Mechanistic and stereochemical studies on Ferrier reaction by means of chirally deuterated glucose

Noriaki Yamauchi, Takumi Terachi, Tadashi Eguchi, Katsumi Kakinuma

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13 Citations (Scopus)

Abstract

The mechanism of Ferrier reaction, cyclitol formation from 5-enopyranosides, was investigated by using (E)-selectively deuterated methyl [6-2H]-2,3,4-tri-O-benzyl-α-D-xylo-hex-5-enopyranoside. The overall reaction was non-stereoselective with respect to the C-6 position of the substrate. Crucial organomercurial intermediates were isolated and characterized. The loss of stereochemical integrity was attributed mainly to the formation of an open-chain organomercurial and its rapid equilibrium. A mechanism involving radical intermediate is suggested.

Original languageEnglish
Pages (from-to)4125-4136
Number of pages12
JournalTetrahedron
Volume50
Issue number14
DOIs
Publication statusPublished - Apr 4 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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