Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-D-glucopyranoside

Tetsuo Tamai; Shingo Asano; Kiichiro Totani; Ken Ichi Takao; Kin Ichi Tadano

doi:10.1055/s-2003-41404

Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-D-glucopyranoside

Tetsuo Tamai, Shingo Asano, Kiichiro Totani, Ken Ichi Takao, Kin Ichi Tadano

Department of Applied Chemistry

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

24 Citations (Scopus)

Abstract

The [3+2] cycloadditions of benzonitrile oxide or pivalonitrile oxide to methyl 4-O-acryloyl-6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-α -D-glucopyranoside provided the respective adducts, each as virtually a single diastereomer. By reductive removal of the carbohydrate template from each adduct, the respective (R)-enriched Δ²-isoxazoline derivative was obtained.

Original language	English
Pages (from-to)	1865-1867
Number of pages	3
Journal	Synlett
Issue number	12
DOIs	https://doi.org/10.1055/s-2003-41404
Publication status	Published - 2003 Jan 1

Keywords

Asymmetric synthesis
Chiral auxiliary
D-glucose
Nitrile oxides

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2003-41404

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title = "Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-D-glucopyranoside",

abstract = "The [3+2] cycloadditions of benzonitrile oxide or pivalonitrile oxide to methyl 4-O-acryloyl-6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-α -D-glucopyranoside provided the respective adducts, each as virtually a single diastereomer. By reductive removal of the carbohydrate template from each adduct, the respective (R)-enriched Δ2-isoxazoline derivative was obtained.",

keywords = "Asymmetric synthesis, Chiral auxiliary, D-glucose, Nitrile oxides",

author = "Tetsuo Tamai and Shingo Asano and Kiichiro Totani and Takao, {Ken Ichi} and Tadano, {Kin Ichi}",

year = "2003",

month = jan,

day = "1",

doi = "10.1055/s-2003-41404",

language = "English",

pages = "1865--1867",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "12",

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TY - JOUR

T1 - Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-D-glucopyranoside

AU - Tamai, Tetsuo

AU - Asano, Shingo

AU - Totani, Kiichiro

AU - Takao, Ken Ichi

AU - Tadano, Kin Ichi

PY - 2003/1/1

Y1 - 2003/1/1

N2 - The [3+2] cycloadditions of benzonitrile oxide or pivalonitrile oxide to methyl 4-O-acryloyl-6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-α -D-glucopyranoside provided the respective adducts, each as virtually a single diastereomer. By reductive removal of the carbohydrate template from each adduct, the respective (R)-enriched Δ2-isoxazoline derivative was obtained.

AB - The [3+2] cycloadditions of benzonitrile oxide or pivalonitrile oxide to methyl 4-O-acryloyl-6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-α -D-glucopyranoside provided the respective adducts, each as virtually a single diastereomer. By reductive removal of the carbohydrate template from each adduct, the respective (R)-enriched Δ2-isoxazoline derivative was obtained.

KW - Asymmetric synthesis

KW - Chiral auxiliary

KW - D-glucose

KW - Nitrile oxides

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U2 - 10.1055/s-2003-41404

DO - 10.1055/s-2003-41404

M3 - Article

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SN - 0936-5214

SP - 1865

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JO - Synlett

JF - Synlett

IS - 12

ER -

Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-D-glucopyranoside

Abstract

Keywords

ASJC Scopus subject areas

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