885703-25-3

Upstream product

• 15896-04-5 1,2-divinylethylene carbonate 
• 35355-33-0 2,3-Dimethylhydroquinone monomethyl ether 

Downstream Products

• 1004530-07-7 C₂₁H₂₄O₃ 
• 1004530-17-9 (4S,5S,E)-methyl 4-hydroxy-5-(4-methoxy-2,3-dimethylphenoxy)hepta-2,6-dienoate 
• 885703-32-2 (5R)-5-((1S,7R,E)-1,7-dihydroxyoct-2-enyl)-4-(phenylsulfonyl)-dihydrofuran-2(3H)-one 
• 885703-35-5 (5R)-5-((1S,7S,E)-1,7-dihydroxyoct-2-enyl)-4-(phenylsulfonyl)-dihydrofuran-2(3H)-one 
• 885703-31-1 (5R)-5-((1S,7R,E)-1,7-dihydroxyoct-2-enyl)-4-(phenylthio)-dihydrofuran-2(3H)-one 
• 885703-34-4 (5R)-5-((1S,7S,E)-1,7-dihydroxyoct-2-enyl)-4-(phenylthio)-dihydrofuran-2(3H)-one 
• 885703-28-6 (S,S)-5-(1-(4-methoxy-2,3-dimethylphenoxy)allyl)furan-2(5H)-one 

Relevant academic research and scientific papers

Readily accessible chiral diene ligands for Rh-catalyzed enantioselective conjugate additions of boronic acids

Enabled by the broad scope of the Pd-catalyzed asymmetric alkylation of meso- and d,l-divinylethylene carbonate, several chiral diene ligands were prepared in two steps from commercial materials. Subsequently, these ligands were evaluated in the Rh-catalyzed asymmetric conjugate addition of boronic acids to enones.

A convergent Pd-catalyzed asymmetric allylic alkylation of dl- And meso-divinylethylene carbonate: Enantioselective synthesis of (+)-australine hydrochloride and formal synthesis of isoaltholactone

The use of a mixture of dl-and meso-divinylethylene carbonate as an electrophile in palladium-catalyzed asymmetric allylic alkylation reactions is reported. From the diastereomeric mixture of meso and chiral racemic starting materials, a single product is obtained in high optical purity employing either oxygen or nitrogen nucleophiles. The resulting dienes have proven to be versatile synthetic intermediates as each carbon is functionalized for further transformation and differentiated by virtue of the reaction. A mechanism for this intriguing transformation is proposed and a concise enantioselective total synthesis of (+)-australine hydrochloride is reported as well as a formal synthesis of isoaltholactone.

Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate

The palladium-catalyzed asymmetric allylic alkylation of a 1:1 mixture of DL- and meso-1,2-divinylethylene carbonate is reported. For the first time, both the ionization and nucleophilic addition steps of the catalytic cycle act as enantiodiscriminating steps to give a single product in high enantiomeric excess. The reactions proceed in >98% ee to efficiently generate useful chiral building blocks from acrolein. The absolute and relative configurations of iso-cladospolide B and 11-epi-iso-cladospolide B were verified by total synthesis, solving an apparent discrepancy in the literature. Copyright