211758-35-9Relevant articles and documents
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.
Asymmetric Diels-Alder reactions of 2-fluoroacrylic acid derivatives. Part 2: A remarkable effect of fluorine substituent on the diastereoselectivity
Ito, Hisanaka,Saito, Akio,Taguchi, Takeo
, p. 1989 - 1994 (2007/10/03)
An efficient construction of a chiral monofluorinated tertiary carbon was achieved by a highly exo- and diastereofacial selective Diels-Alder reaction of a 2-fluoroacrylic acid derivative derived from 8-phenylmenthol, and cyclopentadiene. The substituent effect of the fluorine on the selectivities is remarkable as compared with the other substituents at the α-position of the acrylate.