405292-06-0Relevant academic research and scientific papers
Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides
Nagatsuka, Takayuki,Yamaguchi, Shuhei,Totani, Kiichiro,Takao, Ken-ichi,Tadano, Kin-ichi
, p. 519 - 535 (2007/10/03)
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.
