111265-97-5

Upstream product

• 122977-46-2 2-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-succinic acid 1-methyl ester 
• 121-33-5 vanillin 
• 106-65-0 Dimethyl succinate 
• 111194-04-8 3-methoxycarbonyl-4-(4-hydroxy-3-methoxyphenyl)butanoic acid 

Downstream Products

• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 127951-01-3 (R)-4-[(S)-Benzyloxy-(4-hydroxy-3-methoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 127951-02-4 (R)-4-[(R)-Benzyloxy-(4-hydroxy-3-methoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 127951-00-2 (3R)-(+)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 

Relevant academic research and scientific papers

Efficient Asymmetric Syntheses of Naturally Occurring Lignan Lactones Using Catalytic Asymmetric Hydrogenation as a Key Reaction

Optically pure (R)-arylmethylsuccinic acid mono-methyl esters were obtained efficiently by using the catalytic asymmetric hydrogenation of arylidenesuccinic acid monoesters with a rhodium(I) complex of a chiral bisphosphine, (4S,5S)-MOD-DIOP.Asymmetric total syntheses of some naturally occurring lignans, (+)-collinusin, (-)-deoxypodophyllotoxin, and (+)-neoisostegane, were achieved via several steps from (R)-γ-butyrolactones as key intermediates obtained by reduction of (R)-arylmethylsuccinic acid mono methyl-esters.

Synthesis of efficient chiral bisphosphine ligands, modified DIOPs, (4R,5R)-4-(Diaryl- or dialkylphosphino)methyl-5-(diarylphosphino)methyl-2,2- dimethyl-1,3-dioxolanes, and their use in rhodium(I)-catalyzed asymmetric hydrogenations

Modified DIOPs, (4R,5R)-4-(diaryl- or dialkyphosphino)methyl-5- (diarylphosphino)methyl-2,2-dimethyl-1,3-dioxolanes, were prepared on the basis of our design concept, and used as ligands for the rhodium(I)-catalyzed asymmetric hydrogenations of ketopantolactone, itaconic acid, dimethyl itaconate, and β-aryl-substituted itaconic acid derivatives. A neutral rhodium(I)-complex of (4R-trans)-dicyclohexyl[[5- [(diphenylphosphino)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]phosphine (DIOCP) bearing both a dicyclohexylphosphino group and a diphenylphosphino group was found to be a more efficient catalyst than the original DIOP in the asymmetric hydrogenation of ketopantolactone. Modified DIOPs bearing electron-donating groups at their para positions were efficient ligands for the rhodium(I)-catalyzed assymetric hydrogenations of itaconic acid and its derivatives; in particular, (4R-trans)-[(2,2-dimethyl-1,3-dioxolane-4,5- diyl)bis(methylene)]bis[bis(4'-methoxy-3',5'-dimethylphenyl)phosphine] (MOD- DIOP) bearing both a p-methoxy group and two m,m'-methyl groups on each phenyl group showed much higher enantioselectivity and catalytic activity than DIOP.

HIGHLY EFFICIENT ASYMMETRIC HYDROGENATION OF ITACONIC ACID DERIVATIVES CATALYZED BY A MODIFIED DIOP-RHODIUM COMPLEX

A modified DIOP analogue bearing 4-methoxy and 3,5-dimethyl groups on each phenyl group has been synthesized.The rhodium complex of the ligand has been found to give very high optical yields in the asymmetric hydrogenation of itaconic acid and its derivatives bearing β-aryl groups, the products of which are key-intermediates for optically active lignan derivatives.

THE SYNTHESES OF (R)-(+)-β-VANILLYL-γ-BUTYROLACTONE AND OF CHIRAL LIGNANS THEREFROM

(R)-(+)-β-vanillyl-γ-butyrolactone was obtained in 4 steps including a resolution, from vanillin and dimethyl succinate, and was used for the total syntheses of 5 naturally occurring and optically active lignans such as (+)-isolariciresinol 20.