Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

Mitsuru Shindo, Tomoyuki Sugioka, Kozo Shishido

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF 3 mediated lithium acetylide provided either the α- or β-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO 4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the β- and α-products, respectively.

Original languageEnglish
Pages (from-to)9265-9268
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number50
DOIs
Publication statusPublished - Dec 6 2004
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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