173433-57-3

Upstream product

• 1351987-18-2 butyl-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate 
• 1351987-21-7 methyl-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate 
• 172900-75-3 4-methoxy-3-(3-methoxypropoxy)benzaldehyde 
• 109-19-3 butyl isovalerate 
• 1351987-19-3 C₂₁H₃₄O₆ 
• 1351987-20-6 C₂₁H₃₂O₅ 
• 325154-22-1 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid 
• 172900-73-1 4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene 
• 621-59-0 isovanillin 
• 387868-07-7 (E)-2-(4-methoxy-3-(3-methoxypropoxy)-benzylidene)-3-methylbutanoic acid 
• 953389-95-2 (S)-2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid tert-butylamine salt 
• 656241-29-1 (S)-4-Benzyl-3-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyryl}-oxazolidin-2-one 
• 172900-74-2 [4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol 
• 148433-01-6 3-(3-bromopropoxy)-4-methoxybenzaldehyde 

Downstream Products

• 910546-52-0 (S)-methyl-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate 
• 656241-34-8 (2R)-3,6-diethoxy-2,5-dihydro-2-{(2R)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-pyrazine 
• 656241-30-4 (2S)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl bromide 
• 173433-56-2 (S)-2-(3-(3-methoxypropoxy)-4-methoxybenzyl)-3-methylbutan-1-ol 

Relevant academic research and scientific papers

A Novel Class of Ferrocenyl-Aryl-Based Diphosphine Ligands for Rh- And Ru-Catalysed Enantioselective Hydrogenation

A series of diphosphines of the novel Walphos ligand family all based on a phenylferrocenylethyl backbone were synthesised in a four-step sequence. In the rhodium- or ruthenium-catalysed asymmetric hydrogenation of olefins and ketones enantioselectivities of up to 95% and 97%, respectively, were obtained. A 2-isopropylcinnamic acid derivative of industrial interest was hydrogenated in 95% ee and with turnover numbers of > 5000.

Convergent Synthesis of the Renin Inhibitor Aliskiren Based on C5-C6 Disconnection and CO2H-NH2 Equivalence

A novel synthesis of the renin inhibitor aliskiren based on an unprecedented disconnection between C5 and C6 was developed, in which the C5 carbon acts as a nucleophile and the amino group is introduced by a Curtius rearrangement, which follows a simultaneous stereocontrolled generation of the C4 and C5 stereogenic centers by an asymmetric hydrogenation. Operational simplicity, step economy, and a good overall yield makes this synthesis amenable to manufacture on scale.

Walphos versus biferrocene-based walphos analogues in the asymmetric hydrogenation of alkenes and ketones

Two representative Walphos analogues with an achiral 2,2″- biferrocenediyl backbone were synthesized. These diphosphine ligands were tested in the rhodium-catalyzed asymmetric hydrogenation of several alkenes and in the ruthenium-catalyzed hydrogenation of two ketones. The results were compared with those previously obtained on using biferrocene ligands with a C 2-symmetric 2,2″-biferrocenediyl backbone as well as with those obtained with Walphos ligands. The application of one newly synthesized ligand in the hydrogenation of 2-methylcinnamic acid gave (R)-2-methyl-3- phenylpropanoic acid with full conversion and with 92% ee. The same ligand was used to transform 2,4-pentanedione quantitatively and diastereoselectively into (S,S)-2,4-pentanediol with 98% ee.

Biferrocene-based diphosphine ligands: Synthesis and application of walphos analogues in asymmetric hydrogenations

A total of four biferrocene-based Walphos-type ligands have been synthesized, structurally characterized, and tested in the rhodium-, ruthenium- and iridium-catalyzed hydrogenation of alkenes and ketones. Negishi coupling conditions allowed the biferrocene backbone of these diphosphine ligands to be built up diastereoselectively from the two nonidentical and nonracemic ferrocene fragments (R)-1-(N,N-dimethylamino)ethylferrocene and (SFc)-2- bromoiodoferrocene. The molecular structures of (SFc)-2- bromoiodoferrocene, the coupling product, two ligands, and the two complexes ([PdCl2(L)] and [RuCl(p-cymene)(L)]PF6) were determined by X-ray diffraction. The structural features of complexes and the catalysis results obtained with the newly synthesized biferrocene-based ligands were compared with those of the corresponding Walphos ligands.

ChenPhos: Highly modular P-stereogenic C1-symmetric diphosphine ligands for the efficient asymmetric hydrogenation of α-substituted cinnamic acids

These cats are purrfectionists: The ChenPhos ligands (see structure) showed dramatically higher catalytic activity in the title reaction than their C 2-symmetric predecessor with two dimethylaminoethyl-substituted ferrocenyl(phenyl)phosphanyl groups. The ready accessibility, extreme air stability, and high enantioselectivity, activity, and productivity of these ligands make them very promising for a wide range of practical applications. Copyright

Process for Producing Aliskiren

A new route of synthesis of the compound Aliskiren of formula (I), used in the treatment of hypertension, is described.

PROCESS FOR PRODUCING ALISKIREN

A new route of synthesis of the compound Aliskiren of formula (I), used in the treatment of hypertension, is described.

BIS(FERROCENYLPHOSPHINO) FERROCENE LIGANDS USED IN ASSYMETRIC HYDROGENATION REACTIONS

Abstract Compounds of the formula (I) in the form of racemates, enantiomerically pure diastereomers or a mixture of diastereomers, where the radicals R1 are identical or different and are each C1-C4-alkyl; m is 0 or an integer from 1 to 4; n is 0 or an integer from 1 to 3; p is 0 or an integer from 1 to 5; R2 is an aromatic hydrocarbon radical or a C-bonded heterohydrocarbon radical and R3 is an aliphatic or C-bonded heteroaliphatic hydrocarbon radical; R2 and R3 are identical or different and are each an aliphatic or C-bonded heteroaliphatic hydrocarbon radical; R4 is an unsubstituted or C1-C6-alkyl-, C1-C6-alkoxy- or halogen-substituted hydrocarbon radical; and A is a secondary amino group, are ligands for metal complexes which are suitable as catalysts for homogeneous enantioselective hydrogenation.

Synthesis of enantiopure (R)-2-(4-methoxy-3-(3-methoxypropoxy)-benzyl)-3-methylbutanoic acid-a key intermediate for the preparation of Aliskiren

The enantioselective hydrogenation of (E)-2-(4-methoxy-3-(3-methoxypropoxy)-benzylidene)-3-methylbutanoic acid (1) to (R)-2-(4-methoxy-3-(3-methoxypropoxy)-benzyl)-3-methylbutanoic acid (2)-a key intermediate in the synthesis of the pharmacologically important renin inhibitor Aliskiren-is described. The stereochemistry of the catalytic transformation has been studied using a number of homogeneous chiral Rh(I) and Ru(II) complexes bearing ferrocene-based phosphine ligands. The highest enantioselectivity for the homogeneous hydrogenation of 1 (up to 95% ee) was achieved with a [Rh(NBD)2]BF4 pre-catalyst (substrate/catalyst ratio 100:1, 10 bar H2, 40 °C, in MeOH). To bring the enantioselectivity to perfection an effective method for the isolation of the enantiopure carboxylic acid is suggested likewise.

FERROCENEDIPHOSPHINES

Compounds of the formula I in the form of enantiomerically pure diastereomers or a mixture of diastereomers, (I), where the radicals R1 are identical or different and are each C1-C4-alkyl; m is 0 or an integer from 1 to 3; n is 0 or an integer from 1 to 4; R2 is a hydrocarbon radical or a C-bonded heterohydrocarbon radical; Cp is unsubstituted or C1-C4-alkyl-substituted cyclopentadienyl; Y is a C-bonded chiral group which directs metals of metallation reagents into the ortho position; and Phos is a P-bonded P(III) substituent. The compounds are chiral ligands for complexes of transition metals which are used as homogeneous catalysts in asymmetric syntheses.