22887-55-4

Upstream product

• 150-30-1 Phenylalanine 
• 122-01-0 4-chloro-benzoyl chloride 
• 68319-20-0 N-(4-Chlorbenzyl)-DL-phenylalanin 
• 59490-33-4 N-(4-chloro-benzoylamino)-phenylalanine 

Downstream Products

• 22887-59-8 2-Benzyl-2-(p-chlor-benzamido)-3-dimethylamino-propionsaeure 
• 59490-38-9 N-(p-chlorobenzoyl)phenylalanine methyl ester 
• 1429035-14-2 4-benzyl-2-(4-chlorophenyl)-4-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(phenyl)methyl)oxazol-5(4H)-one 
• 1236384-64-7 N-(3-benzyl-2-oxo-4,6-diphenyl-3,4-dihydro-2H-pyran-3-yl)-4-chlorobenzamide 

Relevant academic research and scientific papers

Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis

The first enantioselective method for the installation of the SCF3 group at the C-4 position of azlactones is described in the present communication under quinidinium phase transfer catalysis. The higher performance of substrates containing electron-rich 2-aryl groups at the azlactone was rationalized using DFT calculations.

Rational Design of 2-Substituted DMAP- N-oxides as Acyl Transfer Catalysts: Dynamic Kinetic Resolution of Azlactones

A novel concept that conversion of chiral 2-substituted DMAP into its DMAP-N-oxide could significantly enhance the catalytic activity and still be used as an acyl transfer catalyst is presented. A new type of chiral 2-substituted DMAP-N-oxides, derived from l-prolinamides, has been rationally designed, facilely synthesized, and applied in the dynamic kinetic resolution of azlactones. Using simple MeOH as the nucleophile, various l-amino acid derivatives were produced in high yields (up to 98% yield) and enantioselectivities (up to 96% ee). Furthermore, α-deuterium labeled l-phenylalanine derivative was also obtained. Experiments and DFT calculations revealed that in 2-substituted DMAP-N-oxide, the oxygen atom acted as the nucleophilic site and the N-H bond functioned as the H-bond donor. High enantioselectivity of the reaction was governed by steric factors, and the addition of benzoic acid reduced the activation energy by participating in the construction of a H-bond bridge. The theoretical chemical study indicated that only when attack directions of the chiral catalyst were fully considered could the correct calculation results be obtained. This work paves the way for the utilization of the C2 position of the pyridine ring and the development of chiral 2-substituted DMAP-N-oxides as efficient acyl transfer catalysts.

Catalytic, Enantioselective α-Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation

A palladium(II)-catalyzed enantioselective α-alkylation of azlactones with nonconjugated alkenes is described. The reaction employs a chiral BINOL-derived phosphoric acid as the source of stereoinduction, and a cleavable bidentate directing group appended to the alkene to control the regioselectivity and stabilize the nucleopalladated alkylpalladium(II) intermediate in the catalytic cycle. A wide range of azlactones were found to be compatible under the optimal reaction conditions to afford products bearing α,α-disubstituted α-amino-acid derivatives with high yields and high enantioselectivity.

Enantioselective synthesis of pyrano[2,3-: C] pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

An enantioselective [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones has been successfully developed through a squaramide catalysis strategy. This protocol provides an efficient and mild access to obtain pyrano[2,3-c]pyrrole scaffolds containing contiguous quaternary and tertiary stereogenic centers in excellent yields (up to 99%) with high levels of diastereo- and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the observed stereoselectivity.

Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.

Bifunctional squaramide-catalyzed synthesis of chiral dihydrocoumarins via ortho-quinone methides generated from 2-(1-tosylalkyl)phenols

A bifunctional squaramide-catalyzed reaction of azlactones with o-quinone methides in situ generated from 2-(1-tosylalkyl)-phenols has been successfully developed under basic conditions, providing an efficient and mild access to chiral dihydrocoumarins bearing adjacent tertiary and quaternary stereogenic centers in high yields with excellent diastereo- and enantioselectivities.

Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(iii)-complex catalyzed inverse-electron-demand hetero-Diels-Alder reaction

An asymmetric inverse-electron-demand hetero-Diels-Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved efficiently by using a chiral N,N′-dioxide-Sc(iii) complex as the catalyst. The desired products were obtained in high yields with excellent enantioselectivities and diastereoselectivities (up to 94% yield, 96% ee and >19:1 dr) under mild reaction conditions. A concerted reaction pathway was confirmed by Operando IR and control experiments.

Bronsted acid accelerated Pd-catalyzed direct asymmetric allylic alkylation of azlactones with simple allylic alcohols: A practical access to quaternary allylic amino acid derivatives

A Bronsted acid accelerated Pd-catalyzed asymmetric allylic alkylation of azlactones with simple allylic alcohols under mild reaction conditions has been realized, which provides a direct and readily scalable approach for the synthesis of all-carbon quaternary allylic amino acid derivatives in excellent yields and good enantioselectivities. (Chemical Equation Presented).

Organocatalyzed asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones: Synthesis of α,α-disubstituted α-amino acid derivatives

The first asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones catalyzed by cinchona alkaloid derived bifunctional thiourea catalysts was developed. A series of α,α-disubstituted α-amino acid derivatives bearing a quaternary stereocenter at the α-position were obtained in high yields with excellent diastereo- and enantioselectivities (up to -20:1 dr and 99% ee). In addition, the trichloromethyl moiety in these adducts was identified as a good leaving group.

Asymmetric synthesis of 3, 4-diaminochroman-2-ones promoted by guanidine and bisguanidium salt

A highly enantioselective synthesis of 3,4-diaminochroman-2-ones has been realized via the domino reaction of o-hydroxy aromatic aldimines and azlactones. Notably, a cis-product was obtained as the major product by the use of guanidine 2a whereas a trans-product was the major product with bisguanidium salt 3·HBArF 4. In two cases, various substituted 3,4-dihydrocoumarins were obtained with high yields (up to 99%) as well as excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >99:1 cis:trans and 98:2 trans:cis, respectively) under mild reaction conditions.