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

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

Access to Document

10.1081/CAR-100108271

Fingerprint Dive into the research topics of 'Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides'. Together they form a unique fingerprint.

Cite this

@article{840463373d404030a04a7faa9f5daeb9,

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}",

year = "2001",

month = nov,

day = "30",

doi = "10.1081/CAR-100108271",

language = "English",

volume = "20",

pages = "519--535",

journal = "Journal of Carbohydrate Chemistry",

issn = "0732-8303",

publisher = "Taylor and Francis Ltd.",

number = "7-8",

}

TY - JOUR

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

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.

UR - http://www.scopus.com/inward/record.url?scp=0035527791&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035527791&partnerID=8YFLogxK

U2 - 10.1081/CAR-100108271

DO - 10.1081/CAR-100108271

M3 - Article

AN - SCOPUS:0035527791

VL - 20

SP - 519

EP - 535

JO - Journal of Carbohydrate Chemistry

JF - Journal of Carbohydrate Chemistry

SN - 0732-8303

IS - 7-8

ER -