23864-91-7

Upstream product

• 125741-54-0 (E)-N'-(2-hydroxybenzylidene)-4-methoxybenzohydrazide 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 100969-61-7 N'-(2-hydroxybenzylidene)-2-(4-methoxyphenyl)acetyl hydrazide 
• 52898-49-4 4,N-dimethoxy-N-methylbenzamide 
• 35822-58-3 2-bromobenzaldehyde diethyl acetal 
• 57591-01-2 (2-(hydroxymethyl)phenyl)(4-methoxyphenyl)methanol 

Downstream Products

• 874672-43-2 3‐(4‐methoxyphenyl)isobenzofuran‐1(3H)‐one 
• 21615-74-7 3-(4-methoxyphenyl)phthalide 
• 1311147-15-5 2-benzyl-3-(4-methoxyphenyl)isoindolin-1-one 
• 37459-58-8 3-(4-Methoxyphenyl)-isoindolin-1-on 

Relevant academic research and scientific papers

Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.

Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins

Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.

Phthalides by rhodium-catalyzed ketone hydroacylation

(Chemical Equation Presented) Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO3, OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92-98% ee's. Our study highlights the key role counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(-)-3-n-butylphthalide is also presented.

2,3-Dihydro-5-alkoxy-5-phenyl-5H-imidazo[2,1-a]isoindoles

Novel 2[2-(1,3-diazacycloalk-2-enyl)]benzophenone compounds and novel 1,3-diazacycloalkenyl[2,1-a]isoindole compounds having useful analgesic and psychostimulant properties are prepared inter alia by condensation of o-benzoylbenzaldehydes with aliphatic diamines.