297765-49-2

Upstream product

• 26086-60-2 2-azido-4'-chloroacetophenone 
• 357952-84-2 (S)-(+)-1-(4-Chlorophenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 108-22-5 Isopropenyl acetate 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 2788-86-5 4-Chlorostyrene oxide 
• 861929-21-7 rac-2-azido-1-(4-chlorophenyl)ethanol 
• 179065-35-1 (S)?2?bromo?1?(4′?chlorophenyl)ethanol 
• 2788-86-5 (2S)-2-(4-chlorophenyl)oxirane 

Downstream Products

• 128535-89-7 (S)-(+)-2-amino-1-(p-chlorophenyl)ethanol 
• 1041193-54-7 (S)-1-(4-chlorophenyl)-2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)ethanol 
• 1041193-53-6 (S)?1?(4′?chlorophenyl)?2?(4?phenyl?1H?1,2,3?triazol?1?yl)ethanol 
• 1182843-48-6 (S)-2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-chlorophenyl)ethanol 

Relevant academic research and scientific papers

Stereoselective reduction of 2-azido-1-phenylethanone derivatives by whole cells of marine-derived fungi applied to synthesis of enantioenriched β-hydroxy-1,2,3-triazoles

Several marine-derived fungi were evaluated by the bioreduction of 2-azido-1-phenylethanone 1, and the strains A. sydowii CBMAI 935 and M. racemosus CBMAI 847 were selected for the reduction of 2-azido-1-phenylethanone derivatives 2–4. Whole cells of A. s

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: Application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols

An enantioselective borane-mediated reduction of a variety of 2-haloketones with 10% spiroaminoborate ester 1 as catalyst is described. By a simple basic workup of 2-halohydrins, optically active epoxides are obtained in high yield and with excellent enantiopurity (up to 99% ee). Ring-opening of oxiranes with phenoxides or sodium azide is investigated under different reaction conditions affording nonracemic 1,2-hydroxy ethers and 1,2-azido alcohols with excellent enantioselectivity (99% ee) and in good to high chemical yield. 2011 American Chemical Society.

Microwave-assisted benzyne-click chemistry: preparation of 1H-benzo[d][1,2,3]triazoles

The benzotriazoles were prepared by three-component and two-component microwave-assisted [3+2] cycloadditions of various azides to benzyne, 3-methoxybenzyne, and 4,5-difluorobenzyne. In the three-component reaction, the aryne is generated, in the presence of an azide prepared in situ, by the reaction of an o-(trimethylsilylaryl) triflate with either CsF or KF/18-Crown-6. However, in the two-component reactions, a freshly prepared azide is added to the reaction vessel prior to aryne generation. Good to excellent yields of benzotriazoles were obtained in 15-20 min when the microwave-assisted reactions were carried out at 125 °C. These reaction times are significantly faster than similar reactions carried out using conventional heating.

Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing β-blocker analogues employing click chemistry

(Chemical Equation Presented) Both antipodes of 2-azido-1-arylethanols were synthesized with excellent optical purity via enzymatic reduction of the corresponding α-azidoacetophenone derivatives catalyzed by a recombinant carbonyl reductase from Candida m

Pd-catalyzed oxidative kinetic resolution of 2-azido-1-arylethanols

(-)-Sparteine/ Pd (II) complex in combination with oxygen as a stoichiometric oxidant, catalyses the oxidative kinetic resolution of β-azido alcohols to afford the corresponding chiral 2-azido-1-arylethanols.

Synthesis of enantiopure β-azidoalcohols from their ketoazides by reduction with NaBH4 in the presence of alumina and in situ lipase resolution

An enantioselective synthesis of chiral β-azidoalcohols via the reduction of the corresponding ketoazides with NaBH4 in the presence of moist aluminium oxide followed by an in situ lipase-mediated resolution is described. The efficiency of vari

Application of optically active 1,2-diol monotosylates for synthesis of β-azido and β-amino alcohols with very high enantiomeric purity. Synthesis of enantiopure (R)-octopamine, (R)-tembamide and (R)-aegeline

A very convenient and highly efficient synthesis of near enantiopure β-azido and β-amino alcohols including biologically active substances such as (R)-octopamine, (R)-tembamide and (R)-aegeline from optically active 1,2-diol monotosylates is reported.

Efficient synthesis of optically active 2-azido-1-arylethanols via oxazaboronlidine - Catalysed asymmetric borane reduction

A simple, efficient, stereo- and regio-selective method for the synthesis of optically active 2-azido-1-phenylethanols by asymmetric reduction of 2-azidoacetophenones with in situ generated, oxazaborolidine- borane complexes in THF, is described. This new method appears to be an alternative to the classical methods previously reported.