74963-01-2

Upstream product

• 22835-64-9 α-phenylcinnamyl alcohol 
• 7042-27-5 ethyl 2,3-diphenyloxirane-2-carboxylate 
• 2699-89-0 (Z)-2,3-diphenylprop-2-en-1-ol 
• 91-47-4 (Z)-2,3-diphenylprop-2-enoic acid 
• 1504-52-5 2,3-diphenyl-2-propen-1-ol 
• 91-48-5 (E)-2,3-diphenylpropenoic acid 
• 36854-27-0 methyl (E)-2,3-diphenyl-2-propenoate 
• 101-41-7 benzeneacetic acid methyl ester 
• 103-82-2 phenylacetic acid 
• 13702-35-7 (E)-2,3-diphenyl-propenal 

Downstream Products

• 83026-52-2 methyl (S)-(+)-2,3-diphenyl-2-hydroxypropionate 

Relevant academic research and scientific papers

Vanadium-catalyzed asymmetric epoxidation: Proline-derived hydroxamic acids revisited

Structural features of ligands and substrates affecting enantioselectivity in vanadium(V)-catalyzed epoxidation of allylic alcohols were investigated. For the hydroxamic acid ligands derived from arylhydroxylamines, 2-aryl-substituted allylic alcohols eme

Magnesium chloride (MgCl2) catalyzed highly regioselective C-3 ring opening of 2,3 epoxy alcohols by N-nucleophile

We herein report Magnesium chloride (MgCl2) catalyzed first highly C3-selective ring-opening reaction of various 2,3-epoxy alcohols with assorted N-Nucleophiles and sodium azide to furnish 3-amino-1,2 diols and 3-azido-1,2 diols respectively in high yields under mild reaction conditions. This protocol attributes the use of catalytic amount of Magnesium chloride (MgCl2), simple reaction conditions, practical operation and broad functional group tolerance.

Asymmetric epoxidation of allylic alcohols catalyzed by vanadium-binaphthylbishydroxamic acid complex

A vanadium-binaphthylbishydroxamic acid (BBHA) complex-catalyzed asymmetric epoxidation of allylic alcohols is described. The optically active binaphthyl-based ligands BBHA 2a and 2b were synthesized from (S)-1,1'-binaphthyl-2,2'dicarboxylic acid and N-substituted-O-trimethylsilyl (TMS)-protected hydroxylamines via a one-pot, three-step procedure. The epoxidations of 2,3,3-trisubstituted allylic alcohols using the vanadium complex of 2a were easily performed in toluene with a TBHP water solution to afford (2R)-epoxy alcohols in good to excellent enantioselectivities.

Tungsten-catalyzed asymmetric epoxidation of allylic and homoallylic alcohols with hydrogen peroxide

A simple, efficient, and environmentally friendly asymmetric epoxidation of primary, secondary, tertiary allylic, and homoallylic alcohols has been accomplished. This process was promoted by a tungsten-bishydroxamic acid complex at room temperature with the use of aqueous 30% H2O2 as oxidant, yielding the products in 84-98% ee.

Vanadium-catalyzed asymmetric epoxidation of allylic alcohols in water

Asymmetric V-catalyzed epoxidation of allylic alcohols can be carried out in water with chiral ligands, which incorporate sulfonamide and hydroxamic acid fragments. Furthermore, the reaction, notorious for its ligand-deceleration effect, in water turned into the ligand-accelerated process. By using this aqueous protocol, a range of allylic alcohols were epoxidized with up to 94% ee.

Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation

In this article, we describe the development and preliminary results of our new designed C2-symmetric bis-hydroxamic acid (BHA) ligands and the application of the new ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols as well as homoallylic alcohols. From this success we demonstrate the versatile nature of BHA in the molybdenum catalyzed asymmetric oxidation of unfunctionalized olefins and sulfides.

Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model

(Chemical Equation Presented) Bishydroxamic acid derivatives are used as ligands for a vanadium catalyst in the preparation of epoxy alcohols (see scheme). The methodology uses aqueous tert-butyl hydroperoxide (TBHP) as an achiral oxidant, low catalyst loading, low reaction temperatures (0°C to room temperature), and simple workup procedures. The reaction is applied to the kinetic resolution of a secondary allylic alcohol and the preparation of small epoxy alcohols. R1, R2, R3: alkyl, aryl, H.

Catalytic asymmetric epoxidation

The present invention relates to the synthesis of chiral epoxides via a catalytic asymmetric oxidation of olefins. Additionally, the methodology provides a method of asymmetrically oxidizing sulfides and phosphines. This asymmetric oxidation employs a catalyst system composed of a metal and a chiral bishydroxamic acid ligand, which, in the presence of a stoichiometric oxidation reagent, serves to asymmetrically oxidize a variety of substrates.

Control of enantioselectivity through a hydrogen-bonded template in the vanadium(V)-catalyzed epoxidation of allylic alcohols by optically active hydroperoxides

The vanadium(V)-catalyzed asymmetric epoxidation of primary allylic alcohols by the optically active TADDOL-derived hydroperoxide as the asymmetric controller provides the corresponding (R)-epoxides in up to 72% ee. From this mechanistic study we conclude

Chiral hydroperoxides as oxygen source in the catalytic stereoselective epoxidation of allylic alcohols by sandwich-type polyoxometalates: Control of enantioselectivity through a metal-coordinated template

The epoxidation of allylic alcohols is shown to be efficiently and selectively catalyzed by the oxidatively resistant sandwich-type polyoxometalates, POMs, namely [WZnM2(ZnW9O 34)2]q- [M = OV(IV), Mn(II), Ru(III), Fe(III), Pd(II), Pt(II), Zn(II); q = 10-12], with organic hydroperoxides as oxygen source. Conspicuous is the fact that the nature of the transition metal M in the central ring of polyoxometalate affects significantly the reactivity, chemoselectivity, regioselectivity, and stereoselectivity of the allylic alcohol epoxidation. For the first time, it is demonstrated that the oxovanadium(IV)-substituted POM, namely [ZnW(VO)2(ZnW 9O34)2]12-, is a highly chemoselective, regioselective, and also stereoselective catalyst for the clean epoxidation of allylic alcohols. A high enantioselectivity (er values up to 95:5) has been achieved with [ZnW(VO)2(ZnW9O 34)2]12- and the sterically demanding TADOOL-derived hydroperoxide TADOOH as regenerative chiral oxygen source. Thus, a POM-catalyzed asymmetric epoxidation of excellent catalytic efficiency (up to 42 000 TON) has been made available for the development of sustainable oxidation processes. The high reactivity and selectivity of this unprecedented oxygen-transfer process are mechanistically rationalized in terms of a peroxy-type vanadium(V) template.