Highly stereoselective Lewis acid mediated conjugate radical additions to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4

Ryosuke Munakata; Kiichiro Totani; Ken Ichi Takao; Kin Ichi Tadano

Highly stereoselective Lewis acid mediated conjugate radical additions to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4

Ryosuke Munakata, Kiichiro Totani, Ken Ichi Takao, Kin Ichi Tadano

Department of Applied Chemistry

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

22 Citations (Scopus)

Abstract

The Lewis acid mediated conjugate additions of alkyl radicals to some 4- crotonyl derivatives of methyl α-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a β- chiral butanoic ester.

Original language	English
Pages (from-to)	979-982
Number of pages	4
Journal	Synlett
Issue number	7
Publication status	Published - 2000 Aug 9

Keywords

Asymmetric synthesis
Carbohydrates
Conjugate additions
Radical reactions

ASJC Scopus subject areas

Organic Chemistry

Cite this

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title = "Highly stereoselective Lewis acid mediated conjugate radical additions to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4",

abstract = "The Lewis acid mediated conjugate additions of alkyl radicals to some 4- crotonyl derivatives of methyl α-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a β- chiral butanoic ester.",

keywords = "Asymmetric synthesis, Carbohydrates, Conjugate additions, Radical reactions",

author = "Ryosuke Munakata and Kiichiro Totani and Takao, {Ken Ichi} and Tadano, {Kin Ichi}",

year = "2000",

month = aug,

day = "9",

language = "English",

pages = "979--982",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "7",

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T1 - Highly stereoselective Lewis acid mediated conjugate radical additions to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4

AU - Munakata, Ryosuke

AU - Totani, Kiichiro

AU - Takao, Ken Ichi

AU - Tadano, Kin Ichi

PY - 2000/8/9

Y1 - 2000/8/9

N2 - The Lewis acid mediated conjugate additions of alkyl radicals to some 4- crotonyl derivatives of methyl α-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a β- chiral butanoic ester.

AB - The Lewis acid mediated conjugate additions of alkyl radicals to some 4- crotonyl derivatives of methyl α-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a β- chiral butanoic ester.

KW - Asymmetric synthesis

KW - Carbohydrates

KW - Conjugate additions

KW - Radical reactions

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M3 - Article

AN - SCOPUS:0033931575

SN - 0936-5214

SP - 979

EP - 982

JO - Synlett

JF - Synlett

IS - 7

ER -

Highly stereoselective Lewis acid mediated conjugate radical additions to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4

Abstract

Keywords

ASJC Scopus subject areas

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