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 |
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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 Nov 30 |
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry