528853-66-9

Upstream product

• 5717-41-9 ethyl 2-methylbuta-2,3-dienoate 
• 51608-60-7 phenyl N-tosyl imine 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 

Downstream Products

• 1266677-83-1 C₂₈H₂₅NO₅S 
• 1266677-20-6 C₂₂H₂₅NO₃S 

Relevant academic research and scientific papers

(R) ENANATIOMER OF APLEXONE

R-aplexone, methods of preparing R-aplexone, or aplexone substantially free of its S-stereoisomer are disclosed. Methods of using R-aplexone or a pharmaceutically acceptable salt or solvate thereof to treat and/or prevent disease are disclosed. Methods of preparing 6-substituted tetrahydropyridine motifs with high enantiomeric excess are also disclosed.

Chiral aminophosphines derived from hydroxyproline and their application in allene–imine [4 + 2] annulation

A robust synthetic route from l-hydroxyproline (l-Hyp) to phosphines has established an expandable library of six chiral aminophosphines, which were then applied to the phosphine-catalyzed [4 + 2] allene–imine annulation. The enantioinduction in the annulations—induced by a purely steric effect—were moderate (up to 57% ee). A switch of the reaction site from the γ- to the β′-carbon atom of the allenoate was observed during the annulations performed using sterically demanding chiral phosphines.

SMALL MOLECULES FOR ENDOTHELIAL CELL ACTIVATION

The present invention provides small molecules for endothelial cell activation and compositions thereof and methods of making and using the same

Diversity through a branched reaction pathway: Generation of multicyclic scaffolds and identification of antimigratory agents

A library of 91 heterocyclic compounds composed of 16 distinct scaffolds has been synthesized through a sequence of phosphine-catalyzed ring-forming reactions, Tebbe reactions, Diels-Alder reactions, and, in some cases, hydrolysis. This effort in diversity-oriented synthesis produced a collection of compounds that exhibited high levels of structural variation both in terms of stereochemistry and the range of scaffolds represented. A simple but powerful sequence of reactions thus led to a high-diversity library of relatively modest size with which to explore biologically relevant regions of chemical space. From this library, several molecules were identified that inhibit the migration and invasion of breast cancer cells and may serve as leads for the development of antimetastatic agents.

A promising new catalyst family for enantioselective cycloadditions involving allenes and imines: chiral phosphines with transition metal-CH2-P: linkages

The racemic rhenium-containing phosphine (η5-C5H5)Re(NO)(PPh3)(CH2PPh3) (3) catalyzes the [3+2] cycloaddition of H2C{double bond, long}C{double bond, long}CHCO2Et and

Catalytic asymmetric synthesis of piperidine derivatives through the [4 + 2] annulation of imines with allenes

Although tertiary phosphines have emerged as remarkably versatile nucleophilic catalysts, there has been only very limited progress in achieving asymmetric catalysis with chiral phosphines. In this report, the first highly enantioselective variant of the

An expedient phosphine-catalyzed [4 + 2] annulation: Synthesis of highly functionalized tetrahydropyridines

Ethyl 2-methyl-2,3-butadienoate acts as a 1,4-dipole synthon and undergoes [4 + 2] annulation with N-tosylimines in the presence of an organic phosphine catalyst. The resulting adducts, ethyl 6-substituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates, are formed in excellent yields with complete regioselectivity. Mechanistic reasoning for this new annulation has led to an expansion of the reaction scope by employing ethyl 2-(substituted-methyl)-2,3-butadienoates to give ethyl 2,6-cis-disubstituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates with high diastereoselectivities. Copyright