37791-56-3

Upstream product

• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 6595-28-4 2-azido-1-(4-methoxyphenyl)ethan-1-one 
• 97070-73-0 (R)-(+)-α-Hydroxy-4-methoxybenzeneacetonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 1299491-05-6 (R)-5-(4-methoxyphenyl)-2-phenyloxazoline 
• 62921-42-0 5-(4-methoxyphenyl)-2-phenyl-1,3-oxazole 
• 1823-86-5 N-[2-(4-methoxyphenyl)-2-ketoethyl]benzamide 
• 637-69-4 4-Methoxystyrene 
• 473552-30-6 (R)-1-(4-methoxyphenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 675579-61-0 (R)-1-(4-methoxyphenyl)-2-nitroethanol 
• 341513-45-9 (R)-β-azido-α-(4-methoxyphenyl)ethanol 
• 604808-45-9 (S)-2-(diethylphosphoryloxy)-2-(4-methoxyphenyl)acetonitrile 
• 46084-23-5 (R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

The Synthesis of Homochiral Naturally Occurring Hydroxy Amides

The chiral naturally occurring hydroxy amides, (-)-tembamide and (-)-aegeline has been synthesised in two steps from (R)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile

Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein

Chiral 1,2-amino alcohols are widely represented in biologically active compounds from neurotransmitters to antivirals. While many synthetic methods have been developed for accessing amino alcohols, the direct aminohydroxylation of alkenes to unprotected, enantioenriched amino alcohols remains a challenge. Using directed evolution, we have engineered a hemoprotein biocatalyst based on a thermostable cytochrome c that directly transforms alkenes to amino alcohols with high enantioselectivity (up to 2500 TTN and 90 % ee) under anaerobic conditions with O-pivaloylhydroxylamine as an aminating reagent. The reaction is proposed to proceed via a reactive iron-nitrogen species generated in the enzyme active site, enabling tuning of the catalyst's activity and selectivity by protein engineering.

Enantioselective Henry and aza-Henry reaction in the synthesis of (R)-tembamide using efficient, recyclable polymeric CuII complexes as catalyst

Chiral copper(II) polymeric [H4]salen (salen=bis[(salicylidene) ethylenediaminato]) complexes CuII-1-3 were generated in situ and used as efficient catalysts in the asymmetric Henry and aza-Henry reaction of various aromatic and alip

Synthesis of (R)-tembamide and (R)-aegeline via asymmetric transfer hydrogenation in water

The synthesis of (R)-tembamide and (R)-aegeline via asymmetric transfer hydrogenation involving enantioenriched monosulfonamide-RhCp a - complex in aqueous sodium formate as hydride donor is described.

Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles

Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated

Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives: synthesis of (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine

Catalytic transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives leads to efficient synthesis of β-adrenergic agonists, (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine.

Binolam-AlCl: A two-centre catalyst for the synthesis of enantioenriched cyanohydrin O-phosphates

The enantioselective synthesis of cyanohydrin O-phosphates by using in situ generated bifunctional catalysts (R)- or (S)-3,3′-bis(diethylaminomethyl) -1, 1′-binaphthol-aluminium chloride (binolam-AlCl) is reported. The reaction, which can be described as an overall cyano-O-phosphorylation of aldehydes, has a wide scope and applicability. Evidence is also provided, including ab initio and DFT calculations, in support of supported by the Lewis acid/Bronsted base (LABB) dual role of the catalyst in inducing first the key enantioselective hydrocyanation, which is then followed by O-phosphorylation. A brief screening of the synthetic usefulness of the resulting cyanohydrin O-phosphates unveiles some interesting applications. Among them, chemoselective hydrolysis, reduction and palladium-catalysed nucleophilic allyl substitution, thereby leading to enantiomerically enriched α-O-phosphorylated α-hydroxy esters, β-amino alcohols and γ-cyanoallyl alcohols, respectively. Naturally occurring (-)-tembamide and (-)-aegeline are synthesised accordingly.

Short asymmetric syntheses of bioactive β-aryl ethanolamine derivatives via the highly diastereoselective delta lactol oxy-Michael addition

Short, stereoselective and efficient total syntheses of the bioactive β-aryl ethanolamine derivatives (R)-tembamide, (R)-aegeline and (R)-pronethalol have been achieved using the highly diastereoselective oxy-Michael addition of 'naked' delta lactol anion

Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol

An efficient synthesis of optically active β-azido alcohols from their ketoazides by a one-pot reduction and an in situ lipase resolution protocol is described. The synthetic utility of this procedure has been illustrated by its application in the practic

Stereoselective synthesis of (R)-(-)-denopamine, (R)-(-)-tembamide and (R)-(-)-aegeline via asymmetric reduction of azidoketones by Daucus carota in aqueous medium

A simple and efficient stereoselective synthesis of (R)-denopamine and other naturally occurring hydroxy amides from optically active (R)-2-azido-1-arylethanols, is described for the first time via reduction of the corresponding α-azidoarylketones with en