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

  • Yamauchi N
  • Terachi T
  • Eguchi T
 et al. 
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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. © 1994.

Author-supplied keywords

  • 2H NMR
  • Ferrier reaction
  • labeled compound
  • oxymercuration

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Authors

  • Noriaki Yamauchi

  • Takumi Terachi

  • Tadashi Eguchi

  • Katsumi Kakinuma

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