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 | |
| Publication status | Published - 2001 |
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ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Organic Chemistry
Cite this
Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides. / Nagatsuka, Takayuki; Yamaguchi, Shuhei; Totani, Kiichiro; Takao, Kenichi; Tadano, Kin ichi.
In: Journal of Carbohydrate Chemistry, Vol. 20, No. 7-8, 2001, p. 519-535.Research output: Contribution to journal › Article
}
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, Kenichi
AU - Tadano, Kin ichi
PY - 2001
Y1 - 2001
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
VL - 20
SP - 519
EP - 535
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
SN - 0732-8303
IS - 7-8
ER -