110480-83-6

Usage

Structure

Chiral amino alcohol with a naphthalene group attached to the amino and hydroxyl functional groups

Use in organic synthesis

Chiral auxiliary or resolving agent

Potential use as a chiral ligand

In asymmetric catalysis

Pharmacological properties

Potential use in the development of drugs for the treatment of various medical conditions

Upstream product

• 86217-77-8 Methyl (+/-)-1-(1-naphthyl)aminoacetate hydrochloride 
• 97611-60-4 2-amino-2-(naphthalen-1-yl)acetic acid 
• 111820-05-4 (S)-amino(naphthalen-1-yl)acetic acid 
• 66-77-3 1-naphthaldehyde 
• 142758-91-6 (4R)-4-(1'-naphthyl)oxazolidin-2-one 
• 204851-60-5 (4S)-4-benzyl-3-[(2R)-3-hydroxy-2-(1'-naphthyl)-1-oxopropyl]-2-oxazolidinone 
• 86-87-3 naphth-1-yl acetic acid 
• 899799-12-3 1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-2-(naphthalen-1-yl)ethanone 
• 899799-14-5 2-(S)-azido-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-2-(naphthalen-1-yl)ethanone 
• 204851-70-7 (R)-3-Hydroxy-2-naphthalen-1-yl-propionic acid 
• 1393524-52-1 (1S)-N-(tert-butoxycarbonyl)-1-(1-naphthyl)-2-hydroxyethylamine 
• 826-74-4 1-vinylnaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 1312718-96-9 2-(tert-butyldimethylsilyloxy)-1-(naphthalen-1-yl)ethanone 

Relevant academic research and scientific papers

Structure-Activity Relationships of Benzamides and Isoindolines Designed as SARS-CoV Protease Inhibitors Effective against SARS-CoV-2

Inhibition of coronavirus (CoV)-encoded papain-like cysteine proteases (PLpro) represents an attractive strategy to treat infections by these important human pathogens. Herein we report on structure-activity relationships (SAR) of the noncovalent active-site directed inhibitor (R)-5-amino-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide (2 b), which is known to bind into the S3 and S4 pockets of the SARS-CoV PLpro. Moreover, we report the discovery of isoindolines as a new class of potent PLpro inhibitors. The studies also provide a deeper understanding of the binding modes of this inhibitor class. Importantly, the inhibitors were also confirmed to inhibit SARS-CoV-2 replication in cell culture suggesting that, due to the high structural similarities of the target proteases, inhibitors identified against SARS-CoV PLpro are valuable starting points for the development of new pan-coronaviral inhibitors.

Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions

The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.

Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)-NHC-catalysed asymmetric hydrogenation of 2-oxazolones

An efficient synthesis of optically active 4-substituted 2-oxazolidinones by the ruthenium(ii)-NHC-catalysed asymmetric hydrogenation of 2-oxazolones was developed. Excellent enantioselectivities (up to 96% ee) and yields (up to 99%) were obtained for a variety of substrates, bearing a range of functional groups and useful motifs. The hydrogenation reaction was successfully scaled up to gram scale using low catalyst loading. Moreover, the utility of this methodology was demonstrated by the transformation of the enantioenriched product into the corresponding chiral β-amino alcohol, a bisoxazoline ligand, and the formal synthesis of (-)-aurantioclavine.

Naphthyl-substituted bisoxazoline and pyridylbisoxazoline-copper(I) catalysts for asymmetric allylic oxidation

The synthesis of naphthyl substituted malonyl-derived and pyridine-based bisoxazolines and their applications in the asymmetric allylic oxidation of cyclohexene with t-butyl p-nitroperbenzoate have been performed with much improved reactivity (75% yield)

Palladium(II)-catalyzed enantioselective arylation of α-imino esters

A protocol for Pd(II)-catalyzed asymmetric arylation of N-aryl imino esters has been developed. The method affords a practical and direct access to chiral arylglycine derivatives in good yields and with high enantioselectivities.

A general asymmetric synthesis of phenylglycinols

Hydride reduction and deprotection of siloxymethyl sulfinimines 2 reliably furnished chiral phenylglycinols 1 or 10 in high overall yield and enantiomeric purity.

An efficient synthesis of enantiomerically pure unnatural aryl glycinols and aryl glycines

A quick route to enantiomerically pure unnatural aryl glycinols and aryl glycines has been established based on an asymmetric azidation reaction using a chiral benzosultam auxiliary. The synthesis of aryl glycinols involves three steps starting from aryla

An efficient synthesis of 1-naphthylbis(oxazoline) and exploration of the scope in asymmetric catalysis

Both enantiomers of 1-naphthylglycine were obtained in 99% ee by enzymatic resolution of the corresponding racemic amino acid amide, giving access to the novel ligands (R)- and (S)-naphthylbis(oxazoline). Initial studies provided insight into the scope an

Highly efficient asymmetric access to 1-azaspiro[4.4]nonane skeleton

Vinylogous Mukaiyama aldol type reaction of chiral non-racemic silyloxypyrroles followed by acidic treatment affords an efficient asymmetric access to 1-azaspiro[4.4]nonanes in high diastereoisomeric excess (up to 79%).