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

doi:10.3987/COM-12-S(N)31

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

9 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 language	English
Pages (from-to)	147-153
Number of pages	7
Journal	Heterocycles
Volume	86
Issue number	1
DOIs	https://doi.org/10.3987/COM-12-S(N)31
Publication status	Published - 2012

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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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.",

author = "Takao, {Ken Ichi} and Tomo Miyashita and Nozomi Akiyama and Takuya Kurisu and Kohei Tsunoda and Tadano, {Kin Ichi}",

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AU - Takao, Ken Ichi

AU - Miyashita, Tomo

AU - Akiyama, Nozomi

AU - Kurisu, Takuya

AU - Tsunoda, Kohei

AU - Tadano, Kin Ichi

PY - 2012

Y1 - 2012

N2 - 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.

AB - 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.

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JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

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

Abstract

ASJC Scopus subject areas

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