A novel method for the stereoselective formation of trans bicyclic ketones by way of oxidative radical cyclization

Takashi Takahashi, Satoshi Tomida, Takayuki Doi

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The stereoselective formation of cyanohydrin 4 was achieved by radical cyclization-oxygen trapping reaction of 5 into an intramolecular acrylic nitrile moiety. The cyanohydrin was used for ring closure reaction with a tosylate, providing the bicyclic systems 1 and 2 with a trans ring fusion.

Original languageEnglish
Pages (from-to)644-646
Number of pages3
JournalSynlett
Issue number5
DOIs
Publication statusPublished - 1999 Jan 1
Externally publishedYes

Keywords

  • Bicyclo[4.3.0]nonan-1-one
  • Bicyclo[4.4.0]decan-1-one
  • Cyanohydrin
  • Intramolecular alkylation
  • Oxidative radical cyclization

ASJC Scopus subject areas

  • Organic Chemistry

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