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

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

Research output: Contribution to journalArticle

6 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

Fingerprint

Bearings (structural)
Allylation
Glyceraldehyde
Stereoselectivity
2,4-Dichlorophenoxyacetic Acid
Aldehydes
Sugars
Powders
Zinc
Chlorides
Carbon
erythrose
propylene

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Construction of all-carbon quaternary stereocenters by zinc-mediated barbier-type allylation in aqueous media. / Takao, Kenichi; Miyashita, Tomo; Akiyama, Nozomi; Kurisu, Takuya; Tsunoda, Kohei; Tadano, Kin Ichi.

In: Heterocycles, Vol. 86, No. 1, 2012, p. 147-153.

Research output: Contribution to journalArticle

Takao, Kenichi ; Miyashita, Tomo ; Akiyama, Nozomi ; Kurisu, Takuya ; Tsunoda, Kohei ; Tadano, Kin Ichi. / Construction of all-carbon quaternary stereocenters by zinc-mediated barbier-type allylation in aqueous media. In: Heterocycles. 2012 ; Vol. 86, No. 1. pp. 147-153.
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