13019-37-9

Upstream product

• 2959-96-8 2-phenylglutaric anhydride 
• 101999-42-2 (+/-)-2-phenyl-1,5-pentanediol 
• 152667-62-4 (3-Chloropropyl)phenyl acetic acid 
• 71309-70-1 ((3,4-dihydro-2H-pyran-6-yl)oxy)trimethylsilane 
• 17763-67-6 Phenyl triflate 
• 201230-82-2 carbon monoxide 
• 770-36-5 4-phenylbuta-3-en-1-ol 
• 1198-34-1 2-Phenylcyclopentanone 
• 103-82-2 phenylacetic acid 

Downstream Products

• 13019-38-0 3-bromo-3-phenyl-tetrahydro-pyran-2-one 
• 79333-46-3 ethyl 2-phenyl-5-bromopentanoate 
• 101999-42-2 (+/-)-2-phenyl-1,5-pentanediol 
• 1239919-68-6 (S)-2-phenylpentane-1,5-diol 
• 15990-78-0 5-phenyl-3,4-dihydro-2H-pyran 
• 13019-35-7 3-phenyl-5,6-dihydro-2H-pyran-2-one 
• 102397-26-2 3-phenyl-2H-pyran-2-one 
• 874656-09-4 1-[2-(1H-indol-3-yl)-ethyl]-3-phenyl-piperidin-2-one 
• 874656-10-7 1-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine 

Relevant academic research and scientific papers

Enantioselective Construction of Quaternary Carbon Stereocenter via Palladium-Catalyzed Asymmetric Allylic Alkylation of Lactones

An efficient and practical method for the synthesis of α,α-disubstituted six-membered lactones was developed. Enantioselective construction of quaternary carbon centers by utilizing Pd-catalyzed asymmetric allylic alkylation proved its feasibility.

Regio- and enantioselective Baeyer-Villiger oxidation: Kinetic resolution of racemic 2-substituted cyclopentanones

A kinetic resolution of racemic 2-substituted cyclopentanones via highly regio- and enantioselective Baeyer-Villiger oxidation has been successfully developed. The reaction could afford the normal 6-substituted δ-lactones in up to 98% ee and >19/1 regioselectivity. Meanwhile, the unreacted ketones were recovered in excellent ee values (up to 98%). It represents the best results of the kinetic resolution of racemic 2-substituted cyclopentanones via nonenzymic asymmetric BV oxidation.

Distal-selective hydroformylation using scaffolding catalysis

In hydroformylation, phosphorus-based directing groups have been consistently successful at placing the aldehyde on the carbon proximal to the directing group. The design and synthesis of a novel catalytic directing group are reported that promotes aldehyde formation on the carbon distal relative to the directing functionality. This scaffolding ligand, which operates through a reversible covalent bond to the substrate, has been applied to the diastereoselective hydroformylation of homoallylic alcohols to afford δ-lactones selectively. Altering the distance between the alcohol and the olefin revealed that homoallylic alcohols gives the distal lactone with the highest levels of regioselectivity.

Weak arene C-h×××o hydrogen bonding in palladium-catalyzed arylation and vinylation of lactones

Weak force in action: In the title reaction, the palladium catalyst (see figure, left) uses weak CH×××O hydrogen bonding to control the absolute configuration of the new stereocenter. A similar palladium catalyst (right) used conventional NH×××O hydrogen bonding to guide stereoselection. Copyright

A convenient synthesis of 3-aryl-δ-lactones

Various (±)-3-aryl-δ-lactones have been prepared from the corresponding arylacetic acids. The lithium dianion of the acid is alkylated with 1-bromo-3-chloropropane and the unpurified product is cyclized with DBU in typically ca. 80% yield over both steps.

HIGHLY REGIOSELECTIVE RING-OPENING OF α-SUBSTITUTED CYCLIC ACID ANHYDRIDES CATALYZED BY LIPASE

Lipase Amano P irreversibly catalyzed a ring-opening of α-substituted cyclic acid anhydrides 1 preferentially at the less hindered carbonyl group to give monoesters with high regioselectivity.

Quantitative Correlation between Calculated Molecular Properties and Retention of a Series of Structurally Related Racemates on Cellulose Triacetate

Racemic compounds cionsisting of an alicyclic six-membered ring with a phenyl group attached to the chiral carbon atom have been investigated.The chemical structure of the alicyclic part was varied systematically, in order to establish its influence on the separability of the racemates into their pure enantiomers on cellulose triacetate (CTA).Theoretical investigations, involving conformational analysis and charge distribution, have been undertaken to correlate structural features with chromatographic behaviour.For this class of compounds two major parameters governing the interaction with CTA are the rotational freedom of the bond to the phenyl group and thereby the relative ability to assume the flattest possible conformation, and a negatively charged neighbourhood of the chiral centre.

Ruthenium Complex Catalyzed Regioselective Dehydrogenation of Unsymmetrical α,ω-Diols

Ruthenium complex catalyzed regioselective dehydrogenation of unsymmetrically substituted 1,4- and 1,5-diols in the presence of such a hydrogen acceptor as α,β-unsaturated ketone gave predominantly β-substituted γ-lactones and γ-substituted δ-lactones, respectively.Among the ruthenium complexes, RuH2(PPh3)4 was the most active and selective catalyst and showed high catalytic activity even at 20 deg C.For example, 2,2-dimethyl-1,4-butanediol was quantitatively converted to dihydro-4,4-dimethyl-2(3H)-furanone and dihydro-3,3-dimethyl-2(3H)-furanone in a ratio of 99.6/0.4 in the presence of 4-phenyl-3-buten-2-one (hydrogen acceptor) and a catalytic amount of RuH2(PPh3)4 at 20 deg C.The proposed main factor controlling the regioselectivity is the steric constraints produced by the substituent(s) of a diol at the coordination step of alkoxy group to ruthenium.