60135-02-6

Upstream product

• 100-52-7 benzaldehyde 
• 79-37-8 oxalyl dichloride 
• 91-48-5 (E)-2,3-diphenylpropenoic acid 
• 91-47-4 (Z)-2,3-diphenylprop-2-enoic acid 
• 103-82-2 phenylacetic acid 
• 36854-27-0 methyl (E)-2,3-diphenyl-2-propenoate 
• 36854-27-0 2,3-diphenylacrylic acid methyl ester 

Downstream Products

• 95025-74-4 7-methoxy-2,3-diphenylchroman-4-one 
• 1089288-59-4 2,3t-diphenyl-acrylic acid-(2-hydroxy-ethyl ester) 
• 103398-50-1 1,2-bis-(2,3t-diphenyl-acryloyloxy)-ethane 
• 101789-75-7 2,3t-diphenyl-acrylic acid-(3-hydroxy-propyl ester) 
• 120335-01-5 1.3-bis-(2.3t-diphenyl-acryloyloxy)-propane 
• 95129-25-2 3--2-methyl-3-propyl-propylamin 
• 96710-60-0 1,3-Bis--2-methyl-2-propyl-propan 
• 95129-25-2 (+)-3--2-methyl-2-propyl-propylamin 
• 96710-60-0 (-)-cis,trans-1,3-Bis-<α-phenyl-cinnamoylamino>-2-methyl-2-propyl-propan 
• 96710-60-0 (+)-cis,trans-1,3-Bis-<α-phenyl-cinnamoylamino>-2-methyl-2-propyl-propan 
• 34845-38-0 C₃₀H₂₂O₂S 
• 76441-04-8 3-((E)-2,3-Diphenyl-acryloyl)-2-thioxo-[1,3]thiazinan-4-one 
• 78284-98-7 Tetrahydro-5,6-diphenyl-3-(2-phenylethyl)-2-thioxo-4H-1,3-thiazin-4-on 
• 79457-88-8 (2-Phenylethyl)thiocarbamidsaeure-(trans-α-phenylzimtsaeure)-thioanhydrid 

Relevant academic research and scientific papers

Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes

We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.

Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor

An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.

Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions

Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.

Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes

A RhIII-catalyzed intramolecular oxidative cross-coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo- and stereoselectivity. This method provides an efficient approach to synthesize macrocyclic compounds containing a 1,3-conjugated diene structure.

Novel and practical asymmetric synthesis of β2,3-amino esters using asymmetric Michael addition of chiral amine

A practical method for the synthesis of chiral β2,3-amino esters having various substituents was developed, which is characterized by an asymmetric Michael addition reaction of a chiral lithium amide with trisubstituted (E)-α,β-unsaturated esters. We found that a highly face-selective protonation occurred by the quick addition of water to the enolate intermediate derived from the Michael addition reaction to afford N-protected β2,3-amino esters in moderate to excellent yields. This finding was made possible by the facile preparation of geometrically pure trisubstituted (E)-α,β-unsaturated esters, which was established recently by our group. The subsequent deprotection of the amino group in the Michael adduct by using N-iodosuccinimide (NIS) efficiently provided β2,3-amino esters having various substituents.

Synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles from (hetero)arylacrylic acids

A three-step method for the synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles is described. Easily accessible bis(trimethylsilyl)acetylene and acrylic acid derivatives are used as starting materials for the preparation of mono- and disubstituted 5-(trimethylsilyl)pent-1-en-4-yn-3-ones. Oxidative phthalimidoaziridination of these enynones provides the key 2-acyl-1-phthalimidoaziridines that are further utilized in the thermal expansion of the three-membered ring to furnish the target functionalizable oxazoles.

Pd-catalyzed dehydrogenative aryl-aryl bond formation via double C(sp2)-H bond activation: Efficient synthesis of [3,4]-fused oxindoles

A Pd(0)-catalyzed double cyclization of easily available o-bromoanilides leading to strained [3,4]-fused oxindoles was developed. The reaction proceeded through a highly ordered sequence involving key carbopalladation, 1,4-Pd migration, and C(sp2)-H functionalization steps. (Chemical Equation Presented).

Enantioselective palladium(0)-catalyzed nazarov-type cyclization

A Pd0-catalyzed asymmetric Nazarov-type cyclization is described. The optimized ligand for the reaction incorporates a weakly coordinating pyridine ring into a TADDOL-derived phosphoramidite (TADDOL=α,α,α,α-tetraaryl-1,3-dioxolane-4,5-dimethanol). The reaction leads to the formation of cyclopentenones as single diastereoisomers that incorporate two contiguous asymmetric centers, one tertiary and one an all-carbon-atom quaternary stereocenter, in high yield and optical purity. It is noteworthy that the reaction does not require that substrates should be activated by aryl substituents.

Regio- and diastereoselective cu-mediated trifluoromethylation of functionalized alkenes

α- and β-substituted N,N-diethylacrylamides undergo copper-mediated direct β-trifluoromethylation. The amide moiety acts as a directing group for the regio- and the stereo-controlled introduction of the trifluoromethyl group. The reaction is carried out u

Rh(III)-catalyzed halogenation of vinylic C-H bonds: Rapid and general access to Z-halo acrylamides

Herein, the regio- and stereoselective iodination, along with some examples for the bromination, of readily available acrylamides to access a variety of differently substituted Z-haloacrylic acid derivatives is reported. The reaction proceeds under mild conditions via a Rh(III)-catalyzed C-H-activation/ halogenation mechanism and represents a rare example of a direct halogenation of electron-poor acrylic acid derivatives.