23101-87-3

Upstream product

• 2453-90-9 N-(3,3-diethoxypropyl)phthalimide 
• 70058-19-4 2-((2S)-1-hydroxypropan-2-yl)-1H-isoindole-1,3(2H)-dione 
• 19967-57-8 bromo-2 propanal 
• 1074-82-4 potassium phtalimide 
• 50-00-0 formaldehyd 
• 3485-84-5 N-vinylphthalimide 
• 136918-14-4 phthalimide 
• 105763-33-5 (2R,3R)-2-phthalimidobutane-1,2-diol 
• 201230-82-2 carbon monoxide 
• 32304-36-2 (+/-)N-(2-oxo-thietan-3-yl)-phthalimide 
• 53701-47-6 2-(1,3-dioxoisoindolin-2-yl)propanoyl chloride 
• 85-44-9 phthalic anhydride 
• 4192-28-3 Phth-L-Ala-OH 
• 4306-25-6 (S)-2-phthalimidopropionyl chloride 

Downstream Products

• 29588-83-8 (R)-N-phthaloylalanine 
• 4192-28-3 Phth-L-Ala-OH 
• 82353-61-5 (R)-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2-methyl-pentanethioic acid S-phenyl ester 
• 82353-61-5 (2R,3S,4S)-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2-methyl-pentanethioic acid S-phenyl ester 

Relevant academic research and scientific papers

Highly regioselective hydroformylation of enamides with phosphite ligands

The regioselective hydroformylation of enamides with a catalyst derived from monodentate phosphites and Rh(acac)(CO)2 was studied. In the hydroformylation of N-vinylphthalimide, all the biphenol-based ligands led to the branched aldehyde; the fastest reaction was observed when using a sterically bulky phosphite. The olefins (E)-N-propenylphthalimide, vinylpyrrolidone, vinylcaprolactam and vinylcarbazole were also investigated.

Effector enhanced enantioselective hydroformylation

In this communication, we report rhodium DIMPhos complexes with an integrated DIM-receptor that can bind carboxylate containing effectors and their application in the rhodium catalyzed hydroformylation reaction. The binding of chiral effectors in non-chiral [Rh(DIMPhos)] catalysts does not lead to enantioselective hydroformylation, but the binding of either achiral or chiral effectors can significantly enhance the enantioselectivity induced by the chiral Rh-metal complexes. For example, the supramolecular complex [Rh]/[1S?L3] displays high regio- and enantioselectivity in the hydroformylation of vinyl acetate (72% ee, and b/l >99), whereas in absence of this effector the ee is around 17%.

Supported Cobalt Nanoparticles for Hydroformylation Reactions

Hydroformylation of olefins has been studied in the presence of specific heterogeneous cobalt nanoparticles. The catalytic materials were prepared by pyrolysis of preformed cobalt complexes deposited onto different inorganic supports. Atomic absorption spectroscopy (AAS) measurements indicated a correlation of catalyst activity and cobalt leaching as well as a strong influence of the heterogeneous support on the productivity. These new, low-cost, easy-to-handle catalysts can substitute more toxic, unstable and volatile cobalt carbonyl complexes for hydroformylations on a laboratory scale.

KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation

A method for aerobic oxidation of aldehydes to carboxylic acids has been developed using organic nitroxyl and NOx cocatalysts. KetoABNO (9-azabicyclo[3.3.1]nonan-3-one N-oxyl) and NaNO2 were identified as the optimal nitroxyl and NOx sources, respectively. The mildness of the reaction conditions enables sequential asymmetric hydroformylation of alkenes/aerobic aldehyde oxidation to access α-chiral carboxylic acids without racemization. The scope, utility, and limitations of the oxidation method are further evaluated with a series of achiral aldehydes bearing diverse functional groups.

Iterative asymmetric hydroformylation/Wittig olefination sequence

Over and over again: Various alkenes underwent the title reaction in the presence of rhodium/bis(diazaphospholane) complexes to give γ-chiral α,β-unsaturated carbonyl products (46-96 % yield) with high enantioselectivity (90-99 % ee). Iterative sequences

Rhodium catalyzed hydroformylation with formaldehyde and an external H 2-source

The efficiency of the syngas-free rhodium catalyzed hydroformylation of olefins with formaldehyde can be significantly improved by the addition of hydrogen gas or formic acid.

New tetraphosphorus ligands for highly linear selective hydroformylation of allyl and vinyl derivatives

New tetraphosphorus ligands have been developed and applied in the rhodium-catalyzed regioselective hydroformylation of a variety of functionalized allyl and vinyl derivatives. Remarkably high linear selectivity was obtained by these tetraphosphorus ligands. The ligand that bears strong electron-withdrawing 2,4-difluorophenyl groups is the most effective one in affording linear aldehydes. The Rh/tetraphosphorus ligand catalyst is highly effective to produce linear aldehydes from functionalized allyl derivatives with heteroatoms or aromatic groups directly adjacent to the allyl group. For vinyl derivatives, the ligand is highly linear selective for acrylic derivatives, styrene, vinyl pyridine, and vinyl phthalimide. Linear to branch ratios of 26:1 and 10:1 were obtained for the hydroformylation of styrene and allyl cyanide, respectively. New tetraphosphorus ligands have been developed and applied in the rhodium-catalyzed regioselective hydroformylation of a variety of allyl and vinyl olefins (see scheme). Remarkably high linear selectivities were obtained by these ligands. Linear-to-branch ratios of 26:1 and 10:1 were obtained for the hydroformylation of styrene and allyl cyanide, respectively. Copyright

Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands

Rhodium complexes of diazaphospholane ligands catalyze the asymmetric hydroformylation of N-vinyl carboxamides, allyl ethers, and allyl carbamates; products include 1,2- and 1,3-aminoaldehydes and 1,3-alkoxyaldehydes. Using glass pressure bottles, short reaction times (generally less than 6 h), and low catalyst loading (commonly 0.5 mol %), 20 substrates are successfully converted to chiral aldehydes with useful regioselectivity and high enantioselectivity (up to 99% ee). Chiral Roche aldehyde is obtained with 97% ee from the hydroformylation of allyl silyl ethers. Commonly difficult substrates such as 1,1- and 1,2-disubstituted alkenes undergo effective hydroformylation with 89-97% ee and complete conversion for six examples. Palladium-catalyzed aerobic oxidative amination of allyl benzyl ether followed by enantioselective hydroformylation yields the β3-aminoaldehyde with 74% ee.

Synthesis of novel rhodium phosphite catalysts for efficient and selective isomerization-hydroformylation reactions

New modular H8-BINOL-based phosphite ligands have been synthesized. High activity and regioselectivity has been achieved in the rhodium-catalyzed isomerization-hydroformylation of internal olefins. The active catalysts have been characterized by in situ NMR studies.

The use of nonactivated iminodienophiles in the stereoselective aza-Diels-Alder reaction

This paper describes the preparation of nitrogen-containing bicycles by the aza-Diels-Alder reaction of nonactivated iminodienophiles and cyclopentadiene. Readily available starting materials such as (S)-(-)-lactate and L-amino acids were used for the pre