19242-50-3

Upstream product

• 101-97-3 Ethyl 2-phenylethanoate 
• 109-94-4 formic acid ethyl ester 
• 623-73-4 diazoacetic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 17147-69-2 4-phenylisoxazol-5(2H)-one 
• 643-77-6 fluoro-phenyl-acetic acid ethyl ester 
• 2510-99-8 ethyl 2-phenylpropanoate 
• 492-37-5 hydratropic acid 
• 22286-82-4 2-phenyl-acrylic acid ethyl ester 

Relevant academic research and scientific papers

BOROX catalysis: Self-assembled AMINO-BOROX and IMINO-BOROX chiral Bronsted acids in a five component catalyst assembly/ catalytic asymmetric aziridination

A five-component catalyst assembly/aziridination reaction is described starting from an aldehyde, an amine, ethyl diazoacetate, B(OPh)3, and a molecule of a vaulted biaryl ligand (VAPOL or VANOL). A remarkable level of chemoselectivity was observed since, while 10 different products could have resulted from various reactions between the five components, an aziridine was formed in 85% yield and 98% ee and only two other products could be detected in 3% yield. Studies reveal that the first in a sequence of three reactions is an exceedingly rapid amine-induced assembly of an AMINOBOROX chiral Bronsted acid species from VAPOL and B(OPh)3, which is followed by imine formation from the amine and aldehyde and the concomitant formation of an IMINO-BOROX chiral Bronsted acid and finally the reaction of the imine with ethyl diazoacetate mediated by the IMINO-BOROX catalyst to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity.

Highly active gold-based catalyst for the reaction of benzaldehyde with ethyl diazoacetate

The gold complex [IPrAu(NCMe)]BF4 catalyzes the reaction of ethyl diazoacetate with benzaldehyde to give mixtures of ethyl 3-oxo-3-phenylpropanoate and ethyl 3-hydroxy-2-phenylacrylate in the first example of a group 11 metal-based catalyst for

Synthesis of vinyl and electron-deficient aryl trifluoromethyl sulfides via Csp2?OH bond activation with AgSCF3 and n-Bu4NI/KI

Direct dehydroxytrifluoromethylthiolation of enols and electron-deficient phenols with AgSCF3 in the presence of n-Bu4NI and KI is reported, affording a series of vinyl and aryl trifluoromethyl sulfides in moderate to excellent yields. This work represents a rare example of direct functionalization of Csp2?OH bonds.

Br?nsted acid mediated cyclizations of ortho-aryl(ethynyl)pyrimidines

A high-yielding procedure for the synthesis of 5-aryl-4-(arylethynyl)pyrimidines from easily available 2-aryl-3-hydroxyacrylates is reported. These pyrimidines readily undergo cyclization in strong Br?nsted acids and, depending on the substitution in alky

BTK INHIBITOR

Provided are a series of BTK inhibitors, and specifically disclosed are a compound, pharmaceutically acceptable salt thereof, tautomer thereof or prodrug thereof represented by formula (I), (II), (III) or (IV).

Unusual anion effects in the iron-catalyzed formation of 3-hydroxyacrylates from aromatic aldehydes and ethyl diazoacetate

Due to the lability of one of the CO ligands in irans-[Fe(PNP)(CO) 2Cl]+ this compound is an efficient catalyst for the coupling of a series of aromatic aldehydes with ethyl diazoacetate (EDA), which give, in most cases, selectively 3-hydroxyacrylates rather than β-oxo esters. This reaction is strongly dependent on the nature of the counterion, Whereas with BF4- the reaction proceeds with conversions up to 90%, in the case of the counterions NO3-, CF 3COO-, CF3SO3-, SbF 6-, and BAr'4- [Ar' = 3,5-(CF 3)2C6H3] no reaction took place. In the case of PF6- only up to 20% conversion was achieved. A conceivable mechanism for the coupling of aromatic aldehydes with EDA was established by means of DFT/B3LYP calculations, which allowed the rationalization of both the chemoselectivity and the role of the counterions.

Catalytic asymmetric alkylation of substituted isoflavanones

The asymmetric alkylation of isoflavanones (3-aryl-chroman-4-ones) and protected 3-phenyl-2,3-dihydroquinolin-4(1H)-ones catalyzed by a novel cinchonidine-derived phase transfer catalyst E is reported. This functionalization occurs at the unactivated C3 methine to afford novel products that can easily be functionalized to generate more complex fused ring systems. The process accommodates a variety of isoflavanones and activated electrophiles and installs a stereogenic quaternary center in high yield and with good-to-excellent selectivity. Isoflavanones are a privileged class of natural products with a broad spectrum of biological activities including insecticidal, antimicrobial, antibacterial, estrogenic, antitumor, and anti-HIV activity. 1 Isoflavanones are also precursors for more complex natural products such as pterocarpans and rotenones.1 Given their therapeutic promise, selective strategies to access new classes of isoflavanones and related structures has high value.2 The functionalization of the C3 position could promote beneficial interactions with biological targets of interest. Specifically, an alkylation at C3 can rapidly access new members of the general class of biologically active homoisoflavanones.3