Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides

Takayuki Nagatsuka; Shuhei Yamaguchi; Kiichiro Totani; Ken Ichi Takao; Kin Ichi Tadano

doi:10.1081/CAR-100108271

Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides

Takayuki Nagatsuka, Shuhei Yamaguchi, Kiichiro Totani, Ken Ichi Takao, Kin Ichi Tadano

Department of Applied Chemistry

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

13 Citations (Scopus)

Abstract

The Diels-Alder reactions of a variety of hexopyranosides carrying an acrylic ester with cyclopentadiene were examined. Some acrylic esters provided the cycloaddition products carrying a norbornene carboxylate with a high level of diastereoselectivity. Plausible mechanisms are presented for the cases of a 4-O-acryloyl-6-deoxy-α-D-glucopyranosidic and 2-O-acryloyl-α-D-glucopyranosidic substrates. By reductive removal of the carbohydrate templates from the adducts, either 2S or 2R-enriched 5-norbornene-2-methanol were obtained.

Original language	English
Pages (from-to)	519-535
Number of pages	17
Journal	Journal of Carbohydrate Chemistry
Volume	20
Issue number	7-8
DOIs	https://doi.org/10.1081/CAR-100108271
Publication status	Published - 2001 Nov 30

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.1081/CAR-100108271

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title = "Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides",

abstract = "The Diels-Alder reactions of a variety of hexopyranosides carrying an acrylic ester with cyclopentadiene were examined. Some acrylic esters provided the cycloaddition products carrying a norbornene carboxylate with a high level of diastereoselectivity. Plausible mechanisms are presented for the cases of a 4-O-acryloyl-6-deoxy-α-D-glucopyranosidic and 2-O-acryloyl-α-D-glucopyranosidic substrates. By reductive removal of the carbohydrate templates from the adducts, either 2S or 2R-enriched 5-norbornene-2-methanol were obtained.",

author = "Takayuki Nagatsuka and Shuhei Yamaguchi and Kiichiro Totani and Takao, {Ken Ichi} and Tadano, {Kin Ichi}",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan.",

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T1 - Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides

AU - Nagatsuka, Takayuki

AU - Yamaguchi, Shuhei

AU - Totani, Kiichiro

AU - Takao, Ken Ichi

AU - Tadano, Kin Ichi

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan.

PY - 2001/11/30

Y1 - 2001/11/30

N2 - The Diels-Alder reactions of a variety of hexopyranosides carrying an acrylic ester with cyclopentadiene were examined. Some acrylic esters provided the cycloaddition products carrying a norbornene carboxylate with a high level of diastereoselectivity. Plausible mechanisms are presented for the cases of a 4-O-acryloyl-6-deoxy-α-D-glucopyranosidic and 2-O-acryloyl-α-D-glucopyranosidic substrates. By reductive removal of the carbohydrate templates from the adducts, either 2S or 2R-enriched 5-norbornene-2-methanol were obtained.

AB - The Diels-Alder reactions of a variety of hexopyranosides carrying an acrylic ester with cyclopentadiene were examined. Some acrylic esters provided the cycloaddition products carrying a norbornene carboxylate with a high level of diastereoselectivity. Plausible mechanisms are presented for the cases of a 4-O-acryloyl-6-deoxy-α-D-glucopyranosidic and 2-O-acryloyl-α-D-glucopyranosidic substrates. By reductive removal of the carbohydrate templates from the adducts, either 2S or 2R-enriched 5-norbornene-2-methanol were obtained.

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Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides

Abstract

ASJC Scopus subject areas

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