Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium

Kiyomi Ohba; Yuichi Koga; Sumihiro Nomura; Masaya Nakata

doi:10.1016/j.tetlet.2015.01.054

Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium

Kiyomi Ohba, Yuichi Koga, Sumihiro Nomura, Masaya Nakata

Department of Applied Chemistry

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

14 Citations (Scopus)

Abstract

We developed an efficient synthetic route for functionalized aryl-β-C-glycosides, which are difficult to prepare by conventional methods. An aryl halide having an ester, cyano, or carbonyl group was treated with 2,4,6-triisopropylphenyllithium in the presence of a δ-lactone (Barbier-type reaction conditions) to afford a coupling product. The following deoxygenation gave the desired aryl-β-C-glycoside in good yield.

Original language	English
Pages (from-to)	1007-1010
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.054
Publication status	Published - 2015 Feb 18

Keywords

2 4 6-Triisopropylphenyllithium
Aldonolactone
Barbier-type reaction
C-Glycoside
Halogen-metal exchange reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium",

abstract = "We developed an efficient synthetic route for functionalized aryl-β-C-glycosides, which are difficult to prepare by conventional methods. An aryl halide having an ester, cyano, or carbonyl group was treated with 2,4,6-triisopropylphenyllithium in the presence of a δ-lactone (Barbier-type reaction conditions) to afford a coupling product. The following deoxygenation gave the desired aryl-β-C-glycoside in good yield.",

keywords = "2 4 6-Triisopropylphenyllithium, Aldonolactone, Barbier-type reaction, C-Glycoside, Halogen-metal exchange reaction",

author = "Kiyomi Ohba and Yuichi Koga and Sumihiro Nomura and Masaya Nakata",

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T1 - Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium

AU - Ohba, Kiyomi

AU - Koga, Yuichi

AU - Nomura, Sumihiro

AU - Nakata, Masaya

PY - 2015/2/18

Y1 - 2015/2/18

N2 - We developed an efficient synthetic route for functionalized aryl-β-C-glycosides, which are difficult to prepare by conventional methods. An aryl halide having an ester, cyano, or carbonyl group was treated with 2,4,6-triisopropylphenyllithium in the presence of a δ-lactone (Barbier-type reaction conditions) to afford a coupling product. The following deoxygenation gave the desired aryl-β-C-glycoside in good yield.

AB - We developed an efficient synthetic route for functionalized aryl-β-C-glycosides, which are difficult to prepare by conventional methods. An aryl halide having an ester, cyano, or carbonyl group was treated with 2,4,6-triisopropylphenyllithium in the presence of a δ-lactone (Barbier-type reaction conditions) to afford a coupling product. The following deoxygenation gave the desired aryl-β-C-glycoside in good yield.

KW - 2 4 6-Triisopropylphenyllithium

KW - Aldonolactone

KW - Barbier-type reaction

KW - C-Glycoside

KW - Halogen-metal exchange reaction

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DO - 10.1016/j.tetlet.2015.01.054

M3 - Article

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SN - 0040-4039

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SP - 1007

EP - 1010

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Functionalized aryl-β-C-glycoside synthesis by Barbier-type reaction using 2,4,6-triisopropylphenyllithium

Abstract

Keywords

ASJC Scopus subject areas

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