156038-73-2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 154663-54-4 (Z)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylidene>-2-phenyl-1,3-oxazol-5(4H)-one 
• 154663-57-7 (E)-2-phenyl-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen>-5(4H)-oxazolone 

Downstream Products

• 178232-09-2 (1R,2S,3R,4S)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester 
• 178232-11-6 (1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester 
• 178232-10-5 methyl (1R,2S,3R,4S)-2-benzamido-3-(1,2-dihydroxyethyl)bicyclo[2.2.1]heptane-2-carboxylate 
• 178232-08-1 (1S,2S,3R,4R)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Diels-Alder reactions of (E)-2-Phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxaz olone with heterogeneous catalysts

Diels-Alder reactions of (E)-2-Phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxaz olone with 2,3-dimethylbutadiene, cyclopentadiene, and 2-methyl-1,3-butadiene (isoprene) are catalysed by silica gel and aluminium, titanium, and zinc catalyst supported on silica gel. l conversion and asymmetric induction are obtained with very low percentages of E/Z isomerisation. The best results are obtained with ZnCl2 supported on silica gel, and by carrying out the reaction without a solvent. The stereochemistry of the major cycloadducts has been determined by single crystal X-ray structure determination and AM1 calculations of the corresponding transition structures.

Asymmetric Diels-Alder Reaction of a Chiral Azlactone

The chiral Z-azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde underwent facial diastereoselective Diels-Alder reaction with cyclopentadiene.Catalyst and temperature dependence of the product ratio is described.The absolute configuration of the major compound was established by an X-ray crystallographic analysis.

Study of the Asymmetric Diels-Alder Reaction of a Chiral Azlactone

The chiral Z-azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde underwent diastereoselective Diels-Alder reaction with cyclopentadiene.Catalyst, temperature and solvent dependence of the product ratio is described.