205380-30-9

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 2306-33-4 monoethyl phthalate 
• 85-44-9 phthalic anhydride 

Downstream Products

• 503631-21-8 3-Ethyl-3-hydroxy-2-((R)-2-hydroxy-1-phenyl-ethyl)-2,3-dihydro-isoindol-1-one 
• 503631-23-0 3-Hydroxy-2-((R)-2-hydroxy-1-phenyl-ethyl)-3-isobutyl-2,3-dihydro-isoindol-1-one 
• 1380611-74-4 2-((R)-2-(4-methoxybenzyloxy)-1-phenylethyl)isoindoline-1,3-dione 
• 162083-31-0 (R)-2-(4-methoxybenzyloxy)-1-phenylethanamine 
• 1380611-75-5 (E,1R)-N-[(R)-2-(4-methoxybenzyloxy)-1-phenylethyl]-1,4-diphenylbut-3-en-1-amine 
• 1380611-76-6 (E,1S)-N-[(R)-2-(4-methoxybenzyloxy)-1-phenylethyl]-1,4-diphenylbut-3-en-1-amine 
• 1380611-77-7 (R)-2-[(R, E)-1,4-diphenylbut-3-enylamino]-2-phenylethanol 

Relevant academic research and scientific papers

Titanium Tetrachloride-Mediated Approach to Access 2-Chloro-2-Substituted Isoindolin-1-ones through the Addition of Alkynes to Acyliminium ions

An asymmetric approach to access 2-substituted isoindolin-1-ones 9–11 was developed through TiCl4-mediated addition-chlorination of N,O-acetals 7 a–7 c with terminal alkynes 8. A range of substrates were amenable to this transformation, and the desired substituted isoindolin-1-ones were obtained in moderate to good yields with moderate diastereoselectivities.

Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni's Reagent

This work illustrates a reductive cross-electrophile coupling protocol for trifluoromethylation of alkyl iodides under Cu-catalyzed/Ni-promoted reaction conditions. The use of diboron esters as the terminal reductant allows the effective generation of the alkyl-CF3 products with excellent functional group tolerance and broad substrate scope. A mechanism involving a reaction of alkyl-Cu with Togni's reagent was proposed.

X-ray crystal structures of Enterococcus faecalis thymidylate synthase with folate binding site inhibitors

Infections caused by Enterococcus faecalis (Ef) represent nowadays a relevant health problem. We selected Thymidylate synthase (TS) from this organism as a potential specific target for antibacterial therapy. We have previously demonstrated that species-specific inhibition of the protein can be achieved despite the relatively high structural similarity among bacterial TSs and human TS. We had previously obtained the EfTS crystal structure of the protein in complex with the metabolite 5-formyl-tetrahydrofolate (5-FTHF) suggesting the protein role as metabolite reservoir; however, protein–inhibitors complexes were still missing. In the present work we identified some inhibitors bearing the phthalimidic core from our in-house library and we performed crystallographic screening towards EfTS. We obtained two X-ray crystallographic structures: the first with a weak phthalimidic inhibitor bound in one subunit and 5-hydroxymethylene-6-hydrofolic acid (5-HMHF) in the other subunit; a second X-ray structure complex with methotrexate. The structural information achieved confirm the role of EfTS as an enzyme involved in the folate pool system and provide a structural basis for structure-based drug design.

PYRIMIDINEDIONE COMPOUNDS AGAINST CARDIAC CONDITIONS

Provided are novel pyrimidine dione compounds and pharmaceutically acceptable salts thereof, that are useful for the treatment of hypertrophic cardiomyopathy (HCM) and conditions associated with left ventricular hypertrophy or diastolic dysfunction. The synthesis and characterization of the compounds and pharmaceutically acceptable salts thereof, are described, as well as methods for treating HCM and other forms of heart disease.

Multimetallic iridium-tin (Ir-Sn3) catalyst in N-acyliminium ion chemistry: Synthesis of 3-substituted isoindolinones via intra- and intermolecular amidoalkylation reaction

The multimetallic iridium-tritin (Ir-Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O) 2}] (1) proved to be a highly effective catalyst towards C-OH bond activation of γ-hydroxylactams, leading to a nucleophilic substitution reaction known as the α-amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3-dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3-substituted isoindolinones and 5-substituted pyrrolidin-2-ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir-Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ-hydroxylactam towards the formation of the N-acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.

Switching regioselectivity in the allylation of imines by N-side chain tuning

A spectacular inversion of α- to γ-regioselectivity in the allylzincation of imines can be achieved by fine-tuning of the N-side chain. This approach allows easy preparation of regioisomeric amines, in racemic as well as enantiopure forms. The usefulness of the method is illustrated by the parallel asymmetric syntheses of 2,3- and 2,5-diphenylpyrrolidines.

Studies on the diastereoselective reductive alkylation of (R)-phenylglycinol derived phthalimide: Observation of stereoelectronic effects

Full details of a flexible approach to N-protected (R)-3-alkyl-isoindolin- 1-ones 13 via diastereoselective reductive-alkylation are described, with emphasis on the stereochemical outcome of the key diastereoselective reactions. Additional experiments allowed finding remarkable stereoelectronic effects on the reductive ring-opening reactions.

Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 1: N-acyliminium ion cyclisations with an internal arene nucleophile

A series of chiral non-racemic 5,5- and 5,6-bicyclic lactams is prepared from (R)-phenylglycinol. These are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3:1 diastereoselectivity. From four structures determined by X-ray crystallography, it follows that spiro indenes are formed preferentially with retention of configuration at the spiro carbon atom and spiro naphthalenes with inversion.

A mild, selective, PyBOP mediated procedure for the conversion of primary Amines into phthalimides

A new method for the protection of primary amines or amino alcohols as phthalimides is described. The phthaloyl group is selectively introduced under mild, anhydrous conditions by reacting the amine with 2- (ethoxycarbonyl)benzoic acid activated by PyBOP, followed by the thermally induced cyclization of the resulting phthalamic ester. These reaction conditions are applicable to a variety of primary amines and good yields are obtained in all cases.