129215-12-9

Upstream product

• 586-39-0 1-nitro-3-vinyl-benzene 
• 20697-05-6 2-(3-nitrophenyl)oxirane 
• 4248-19-5 tert-butyl carbazate 
• 51-79-6 urethane 
• 55338-04-0 (+/-)-2-bromo-1-(3-nitrophenyl)ethanol 
• 2227-64-7 3'-nitro-2-bromoacetophenone 
• 13425-36-0 ()-2-chloro-1-(3-nitrophenyl)ethanol 
• 193761-55-6 (R)-2-bromo-1-(3-nitrophenyl)ethan-1-ol 
• 99-47-8 2-chloro-1-(3-nitrophenyl)ethanone 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 1221179-25-4 (R)-2-(N-benzyl-N-(2-(benzyloxy)ethyl)amino)-1-(3-nitrophenyl)ethan-1-ol 
• 776302-75-1 methanesulfonic acid 3-[2-(tert-butoxycarbonyl-{2-hydroxy-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethyl}-amino)-propyl]-1H-indol-7-yl ester 

Relevant academic research and scientific papers

Self-supported chiral polymeric MnIII salen complexes as highly active and recyclable catalysts for epoxidation of nonfunctionalized olefins

Abstract A series of self-supported chiral polymeric MnIII N,N′-ethylenebis(salicylimine) (salen) complexes were synthesized through metalation of the corresponding salen ligands obtained by condensation of several bis/tris-aldehydes with (1R,2

Electronic effects on enantioselectivity in epoxidation catalyzed by D 4-symmetric chiral porphyrins

Asymmetric epoxidation of various aromatic olefins was examined with our D4-symmetric chiral porphyrin. The enantioselectivity was greatly improved upon when the substrates contained electron-deficient groups. Moreover, examination of electroni

Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl) ethanol as a synthetic precursor for (R)-phenylephrine

The incubated whole-cell biocatalyst of Pichia minuta JCM 3622 reduced 2-chloro-1-(3-nitrophenyl)ethanone to provide (R)-2-chloro-1-(3-nitrophenyl) ethanol with 99.2% ee in 87% isolated yield in the presence of Amberlite XAD-7 as a reservoir for the hydrophobic, crystalline and toxic substrate. The product was transformed to (R)-1-(3-hydroxyphenyl)-2-methylaminoethanol (phenylephrine, 1a), a selective α1-adrenergic receptor agonist, in 98.0% ee over five steps.

Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation of alkenes using (2R,3S,4R,5S)-(-)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate

Epoxidation of alkenes by peracid, generated in situ from (2R,3S,4R,5S)-(-)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate [(-)-DIKGA] and hydrogen peroxide by lipase catalysis induces chirality on the product epoxides with moderate to good enantioselectivity (35-71%). Alkoxy/aralkyloxy styrenes however did not undergo any epoxidation. (R)-(+)-4-Hydroxy styrene-7,8-oxide was formed and isolated with moderate enantiomeric excess (57%) but was found to have poor stability.

Dynamic kinetic resolution of racemic β-haloalcohols: Direct access to enantioenriched epoxides

The direct chemo-enzymatic DKR of racemic β-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the haloalcohol is achieved using the new iridacycle 3, one of the most effective racemization catalysts to date for β-haloalcohols. Copyright

A novel method for the synthesis of chiral epoxides from styrene derivatives using chiral acids in presence of Pseudomonas lipase G6 [PSL G6] and hydrogen peroxide

Chiral epoxidation of styrene and its derivatives was carried out using series of chiral acids and urea hydrogen peroxide (UHP) or aqueous hydrogen peroxide (50%) in two phases under the catalytic influence of immobilized Pseudomonas lipase G6 [PSL G6] at 25-55 °C. A moderate to good yield and enantioselectivities of chiral epoxides were obtained.

Chiral styrene oxides from α-haloacetophenones using NaBH4 and TarB-NO2, a chiral Lewis acid

High enantioselectivities are obtained for the preparation of chiral styrene oxides through reduction of α-haloacetophenones using TarB-NO 2 reagent and the inexpensive and mild reducing agent NaBH 4. The epoxides are easily obtained in up to 95% ee through routine acid-base workup of the product alcohols. Either the (R) or (S) epoxide can be obtained by using the appropriate l- or d-tartaric acid starting material in the TarB-NO2 reagent.

Effective asymmetric epoxidation of styrenes by chiral dioxirane

High enantioselectivity (80-92% enantiomeric excess (ee)) has been obtained for the epoxidation of various styrenes using an easily prepared ketone (4) catalyst.

Tryptamine-based human β3-adrenergic receptor agonists. Part 3: Improved oral bioavailability via modification of the sulfonamide moiety

The continued SAR investigation of tryptamine-based human β3-adrenergic receptor (AR) agonists is reported. Prior efforts resulted in the identification of 2 as a potent β3-AR agonist. Further modification of the left side arylsulfonamide portion in 2 provided compounds with good cell permeability, which have potent agonistic activity for β3-AR. Cinnamylamine analog 16i exhibited an excellent agonistic profile in vitro and good oral bioavailability in rats.

Direct catalytic synthesis of enantiopure 5-substituted oxazolidinones from racemic terminal epoxides

(Chemical Equation Presented) A venerable scaffold for asymmetric synthesis and drug development, chiral 5-substituted oxazolidinones are obtained in almost enantiomerically pure form (up to 99.9% ee) starting from racemic terminal epoxides. The salient features of this process include the very simple and convenient experimental protocol and the employment of a readily accessible catalyst and inexpensive, easily handled starting materials. An enantioconvergent approach for the total conversion of racemic epoxide into a single stereoisomeric oxazolidinone is also described.