Construction of all-carbon quaternary stereocenters by zinc-mediated barbier-type allylation in aqueous media

Ken Ichi Takao, Tomo Miyashita, Nozomi Akiyama, Takuya Kurisu, Kohei Tsunoda, Kin Ichi Tadano

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Stereoselective construction of an all-carbon quaternary stereocenter by Barbier-type allylation in aqueous media is described. Sugar-derived aldehydes, 2,3-O-isopropylidene-D-glyceraldehyde and 2,4-O-benzylidene-D-threose, were reacted with geranyl chloride in the presence of zinc powder to provide adducts bearing quaternary stereocenters with good stereoselectivity.

Original languageEnglish
Pages (from-to)147-153
Number of pages7
JournalHeterocycles
Volume86
Issue number1
DOIs
Publication statusPublished - 2012 Dec 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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