211758-35-9

Upstream product

• 95-12-5 (-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol 
• 98-88-4 benzoyl chloride 
• 542-92-7 cyclopenta-1,3-diene 
• 347384-29-6 methyl 4-O-(bicyclo[2.2.1]hept-5-ene-2-carbonyl)-2,3-di-O-t-butyldimethylsilyl-6-deoxy-α-D-glucopyranoside 
• 211448-05-4 4-(1R,2S,5R,3'S,4'S,6'S)-[5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyloxycarbonyl]-4-chlorobicyclo[2.2.1]heptene 

Downstream Products

• 95-12-5 (-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol 

Relevant academic research and scientific papers

Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides

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.

Novel application of chiral micellar media to the Diels-Alder reaction

A novel chiral surfactant has been used in the first reported aqueous chiral micellar catalysis of a Diels-Alder reaction and enantioselectivities have been observed.

Asymmetric Diels-Alder reactions of 2-fluoroacrylic acid derivatives. Part 2: A remarkable effect of fluorine substituent on the diastereoselectivity

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.