63591-85-5

Upstream product

• 103-82-2 phenylacetic acid 
• 524-38-9 N-hydroxyphthalimide 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 87791-64-8 4(S)-methyl-3(S)-(phenylacetamido)-2-azetidinone 
• 102806-25-7 2-(benzyloxy)-1,1′-biphenyl 
• 946-80-5 (benzyloxy)benzene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 329-98-6 phenylmethylsulphonyl fluoride 
• 26087-47-8 iprobenfos 
• 13286-32-3 thiophosphoric acid S-benzyl ester O,O'-diethyl ester 

Relevant academic research and scientific papers

Decarboxylative Radical Addition to Methylideneoxazolidinones for Stereocontrolled Synthesis of Selectively Protected Diamino Diacids

Syntheses of stereochemically pure and selectively protected diamino diacids can be achieved by redox decarboxylation of distal N-hydroxyphthalimide esters of protected aspartic, glutamic or α-aminoadipic acids via radical addition to methylideneoxazolidinones. The products are useful for solid-supported syntheses of robust bioactive carbocyclic peptide analogs. Yields of reactive primary radical addition are superior to those of more stabilized radicals, and the reaction fails if the alkylideneoxazolidinone has a methyl substituent on its terminus (i.e., 13a/13b).

Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids

A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.

Photoinduced Decarboxylative Phosphorothiolation of N-Hydroxyphthalimide Esters

A visible-light-induced protocol for the synthesis of phosphorothioates is developed by employing the Ir-catalyzed decarboxylative phosphorothiolation of N-hydroxyphthalimide esters. This novel synthesis method utilizes carboxylic acids as raw material, which is stable, cheap, and commercially available. Scope studies show that this reaction has good compatibility of functional groups. Notably, both the synthesis of steric hindrance phosphorothioates and the later modification of some bioactive compounds are successfully achieved.

Substrate for synthesizing beta-Se amino acid as well as preparation method and application of substrate

The invention discloses a substrate for synthesizing beta-Se amino acid as well as a preparation method and application of the substrate, and the beta-Se amino acid is almost seldom synthesized by a method except selenocysteine at present. A substrate (namely a formula (I)) for synthesizing beta-Se amino acid is autonomously designed, and different beta-Se amino acids can be obtained only by changing a free radical precursor generated by photoreaction by using a general intermediate (namely the formula (I)) which is newly designed in the invention, so that divergent synthesis of the beta-Se amino acids is realized. According to the method for synthesizing the beta-Se amino acid, synthesis can be simply and efficiently achieved, good functional group compatibility can be achieved, the yield is generally high, and the application range of natural chemical connection is further expanded.

Chemoselective Union of Olefins, Organohalides, and Redox-Active Esters Enables Regioselective Alkene Dialkylation

Multicomponent catalytic processes that can generate multiple C(sp3)-C(sp3) bonds in a single step under mild conditions, particularly those that employ inexpensive catalysts and substrates, are highly sought-after in chemistry research for complex molecule synthesis. Here, we disclose an efficient Ni-catalyzed reductive protocol that chemoselectively merges alkenyl amides with two different aliphatic electrophiles. Starting materials are readily accessible from stable and abundant feedstock, and products are furnished in up to >98:2 regioisomeric ratios. The present strategy eliminates the use of sensitive organometallic reagents, tolerates a wide array of complex functionalities, and enables regiodivergent addition of two primary alkyl groups bearing similar electronic and steric attributes across aliphatic C=C bonds with exquisite control of site selectivity. Utility is underscored by the concise synthesis of bioactive compounds and postreaction functionalizations leading to structurally diverse scaffolds. DFT studies revealed that the regiochemical outcome originates from the orthogonal reactivity and chemoselectivity profiles of in situ generated organonickel species.

Stereoselective and Divergent Construction of β-Thiolated/Selenolated Amino Acids via Photoredox-Catalyzed Asymmetric Giese Reaction

Sulfur and selenium occupy a distinguished position in biology owing to their redox activities, high nucleophilicity, and acyl transfer capabilities. Thiolated/selenolated amino acids, including cysteine, selenocysteine, and their derivatives, play critic

Method for synthesis of beta-S amino acid

The invention discloses application of methyl(R)-2-(tert-butyl)-3-formyl-2, 3-thiazoline-4-methyl formate (I) in preparation of beta-S amino acid (II). According to the invention, the raw materials are simple and easily available, and a universal intermed

METHODS FOR PREPARING A BORONIC ACID OR A BORONIC ESTER

Methods are disclosed for converting a carboxylic acid by using a diboron reagent to convert the carboxylic acid or imide ester derivative of a carboxylic acid to a boronic ester. The method may involve providing an imide ester, such as a phthalimide ester, of a carboxylic acid, and treating the imide ester with a diboron reagent, thereby forming a boronic ester. The diboron reagent may be selected from bis(catecholato)diboron, B2(OH)4 or a mixture thereof, optionally in the presence of catechol.

A visible light-driven minisci-type reaction with N-hydroxyphthalimide esters

A visible light-promoted protocol for the redox-neutral coupling of N-hydroxyphthalimide esters with different N-heterocyclic compounds is described. The reaction proceeds through an alkyl radical intermediate generated by reductive decarboxylation of N-hydroxyphthalimide esters. In contrast to the original Minisci protocol, polyalkylation can largely be avoided. Mechanistic investigations revealed a radical chain mechanism which in some cases can proceed even if no photocatalyst is added. This valuable and functional group-tolerant reaction produces substituted heterocycles in moderate to excellent yield. The use of inexpensive starting materials and LEDs as the light source are key features of this C–C bond formation.