Stereoselective synthesis of (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides by base-promoted ring-opening of iodomethylated epoxides

Takahiro Ichige, Daisuke Matsuda, Masaya Nakata

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Both (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides were stereoselectively synthesized from iodomethylated epoxides by treatment with sodium hexamethyldisilazane in DMF and with LDA in THF (or lithium 2,2,6,6-tetramethylpiperidide in THF), respectively.

Original languageEnglish
Pages (from-to)4843-4848
Number of pages6
JournalTetrahedron Letters
Volume47
Issue number28
DOIs
Publication statusPublished - 2006 Jul 12

Keywords

  • Anti elimination
  • Base-promoted ring-opening
  • Epoxides
  • Syn elimination
  • Vinyl iodides

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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