1073277-36-7

Upstream product

• 108-05-4 vinyl acetate 
• 58824-56-9 1-(p-bromophenyl)prop-2-en-1-ol 
• 22731-70-0 1-(4-bromophenyl)prop-2-en-1-one 
• 2768-02-7 (vinyl)trimethoxylsilane 
• 1122-91-4 4-bromo-benzaldehyde 
• 92-54-6 4-phenyl-1-piperazine 
• 108-22-5 Isopropenyl acetate 
• 97-72-3 2-Methylpropionic anhydride 

Downstream Products

• 1073277-41-4 (S)-(-)-1-(4'-bromophenyl)prop-2-en-1-yl tert-butyl carbonate 
• 1282033-79-7 (1R,2R)-(4-bromophenyl)-2,3-glycidol 

Relevant academic research and scientific papers

Highly efficient kinetic resolution of aryl-alkenyl alcohols by ru-catalyzed hydrogen transfer

No matter through asymmetric reduction of ketones or kinetic resolution of secondary alcohols, enantioselective synthesis of the corresponding secondary alcohols is challenging when the two groups attached to the prochiral or chiral centers are spatially

Method for preparing chiral gamma-amino alcohol and chiral alpha-allyl alcohol by one-pot method

The invention relates to a method for preparing chiral gamma-amino alcohol and chiral alpha-allyl alcohol by a one-pot method. The method comprises the following steps: making a racemic alpha-allyl alcohol compound, an amine compound, a chiral ruthenium complex and an alkaline reagent react in an organic solvent, and carrying out separation and purification after completion of the reaction, so that chiral gamma-aminoalcohols and chiral alpha-allylalcohol are prepared, wherein a chiral ruthenium complex is selected from one of them. According to the preparation method of the chiral compound, two chiral compounds with wide purposes, namely the chiral gamma-amino alcohol and the chiral alpha-allyl alcohol, are obtained at the same time through a one-pot reaction, the reaction is simple, the atom economy is high, few by-products are produced, and the requirements of green chemistry are met.

Copper(I) Diphosphine Bifluoride Complexes as Efficient Preactivated Catalysts for Nucleophilic Addition on Unsaturated Functional Groups

Herein we report the synthesis of a family of copper(I) diphosphine bifluoride complexes, their characterization, and their use as efficient preactivated catalysts for nucleophilic copper addition of pronucleophiles on unsaturations. Their use as mechanistic probes is also highlighted by the identification of two copper deuterides.

Pseudomonas sp. Lipase Immobilized on Magnetic Porous Polymer Microspheres as an Effective and Recyclable Biocatalyst for Resolution of Allylic Alcohols

Magnetic porous polymeric microspheres containing epoxy groups were prepared by suspension polymerization (denoted as magnetic Fe3O4@GEM microspheres). Fe3O4@GEM with a specific surface area of 30.41 m2/g, average pore diameter of 17.13 nm, and pore volume of 0.13 cm3/g exhibited superparamagnetic behavior with the saturation magnetization of 7.1 emu/g. The content of epoxy groups on Fe3O4@GEM was 0.22 mmol/g. Pseudomonas sp. lipase (PSL) was covalently immobilized onto the Fe3O4@GEM microspheres through the reaction between the amino groups of the enzyme and the epoxy groups on the microspheres. PSL/Fe3O4@GEM exhibited enhanced enantioselectivity for the resolution of allylic alcohol to the corresponding optically active (S)-allylic alcohol and (R)-allylic alcohol acetate compared to free PSL. The enantiomeric excess of (S)-l-pheny-2-propen-1-ol for the former (98.1%) was 81.7 times that of the latter (1.2%) when the immobilized PSL was used for transesterification resolution of (R,S)-l-pheny-2-propen-1-ol. Furthermore, the ees and eep values were still retained at 95.2% and 95.4% after PSL/Fe3O4@GEM was recycled 10 times, indicating that PSL/Fe3O4@GEM had very good reusability. In addition, the transesterification resolution of (R,S)-1-(4-methylphenyl)-2-propen-1-ol and (R,S)-1-(4-bromophenyl)-2-propen-1-ol was catalyzed by PSL/Fe3O4@GEM, affording ideal ees and eep values of 99.3%, 97.4% and 99.6%, 98.2%, respectively. Therefore, PSL/Fe3O4@GEM demonstrated its potential as a highly efficient enzymatic reactor and Fe3O4@GEM would be very promising carriers for immobilizing enzymes in industrial application.

Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols

The non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.

Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade

Styrene monooxygenase (SMO) can catalyze the kinetic resolution of secondary allylic alcohols to provide enantiopure glycidol derivatives. To overcome the low theoretical yield of kinetic resolution, we designed a one-pot two-step enzymatic cascade using prochiral α,β-unsaturated ketones as the substrates. An S-specific ketoreductase ChKRED03 was screened for the efficient bioreduction of the substrates to provide (S)-allylic alcohols, which underwent SMO-catalyzed epoxidation to achieve glycidol derivatives with contiguous stereogenic centers. Excellent enantioselectivity (ee > 99%) and diastereoselectivity (de > 99%) were achieved for the majority of the substrates, and product yields reached up to >99%. This journal is

Kinetic resolution of allylic alcohols via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic allylic alcohols has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 968. Substituent effect is briefly discussed.

Highly diastereo- and enantio-selective epoxidation of secondary allylic alcohols catalyzed by styrene monooxygenase

Enantiomerically enriched glycidol derivatives with contiguous stereogenic centers were obtained in a highly diastereo- and enantio-selective epoxidation catalyzed with the styrene monooxygenase StyAB2.

Chiral phosphonite, phosphite and phosphoramidite η6-arene- ruthenium(ii) complexes: Application to the kinetic resolution of allylic alcohols

The synthesis and characterization of chiral arene-ruthenium complexes [RuCl2(η6-arene){(R)-PR(binaphthoxy)}] (arene = benzene (1), p-cymene (2), mesitylene (3); R = Ph (a), OPh (b), piperidyl (c)) are described. Derivatives 1-3 have been employed to promote the kinetic resolution of allylic alcohols through a redox-isomerization process. As a general trend, the best selectivities are attained with the more sterically hindered catalysts i.e. those containing p-cymene or mesitylene ligands. The Royal Society of Chemistry 2010.

Synthesis of enantiopure 1-arylprop-2-en-1-ols and their tert-butyl carbonates

(Chemical Equation Presented) Enantiomerically pure 1-arylpropenols 8 have been prepared by resolution of the corresponding racemates, using the lipase formulation Novozyme 435. Deprotonation of the latter alcohols with n-BuLi, followed by derivatization with (t- BuO)2CO, afforded the corresponding carbonates 5. Optimization of the process is presented.