Generation of 2-substituted 2-metallo-1,3-dithiane derivatives and their coupling with 2,3-disubstituted oxiranes

Mitsuaki Ide, Masaya Nakata

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3 Citations (Scopus)

Abstract

2-Substituted 2-lithio-1,3-dithiane derivatives have been used as an excellent acyl anion equivalent for carbon-carbon bond formation. One of the representative examples is their coupling with monosubstituted oxiranes. We found that 2-substituted 1,3-dithiane derivatives were lithiated with n-BuLi at room temperature and the resulting anions reacted with 2,3-disubstituted oxiranes at room temperarure, giving the coupling products in satisfactory yield. This type of coupling reaction has not been used in natural product syntheses, because the temperature-dependent instability of dithianide anions and the poor electrophilicity of 2,3-disubstituted oxiranes should be discouraging factors. This article describes effective metallation conditions of 2-substituted 1,3-dithiane derivatives and the practical synthesis of four stereoisomers of bis-propionates via the dithiane coupling with oxiranes.

Original languageEnglish
Pages (from-to)857-867
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume58
Issue number9
Publication statusPublished - 2000 Sep

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Keywords

  • Bis-propionates
  • Coupling reactions
  • Dibutylmagnesium
  • Dithianes
  • Oxiranes
  • Stereoselective reduction

ASJC Scopus subject areas

  • Organic Chemistry

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