4361-50-6

Upstream product

• 50-00-0 formaldehyd 
• 115051-47-3 2-hydroxy-2-phenyl-propionaldehyde-oxime 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 98-86-2 acetophenone 
• 97006-89-8 (1,2-Dihydroxy-2-phenyl-propyl)-phosphonic acid diethyl ester 
• 4217-66-7 1,2-dihydroxy-2-phenylpropane 
• 40962-69-4 (E)-diethyl (2-phenylprop-1-en-1-yl)phosphonate 
• 34713-70-7 2-Phenylpropanal 
• 2406-22-6 (R)-1-phenyl-1,2-ethanediol 
• 682351-17-3 (R)-2-hydroxy-2-phenylpropanal dimethyl acetal 
• 862669-01-0 2-fluoro-2-phenylpropionaldehyde 
• 1034980-22-7 C₁₆H₁₄O₂ 
• 100-58-3 phenylmagnesium bromide 
• 156365-90-1 (2S,4S,5R)-2-(1R)-(1-hydroxy-1-phenyl)ethyl-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine 

Downstream Products

• 98-86-2 acetophenone 
• 1456505-51-3 (R+S)-5-methyl-3-((1r,4R)-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexyl)-5-phenyloxazolidin-2-one 
• 1456507-57-5 1-((1r,4r)-4-((2-hydroxy-2-phenylpropyl)amino)cyclohexyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one 
• 1456507-59-7 1-((1r,4r)-4-((2-hydroxy-2-phenylpropyl)amino)cyclohexyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbonitrile 
• 1456507-11-1 1-((1r,4r)-4-((2-hydroxy-2-phenylpropyl)amino)cyclohexyl)-1H-benzo[d]imidazol-2(3H)-one 
• 4217-66-7 1,2-dihydroxy-2-phenylpropane 
• 1365175-97-8 (S,E)-3-hydroxy-3-phenylbut-1-en-1-yl propionate 
• 13113-71-8 (S)-Atrolactic acid 
• 2406-22-6 (2S)-2-phenylpropane-1,2-diol 
• 2406-22-6 (R)-1-phenyl-1,2-ethanediol 
• 3966-30-1 (R)-Atrolactic acid 
• 13448-80-1 methyl R-(-)-atrolactate 

Relevant academic research and scientific papers

Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C2-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary

The synthesis and diastereoselective performance of the pseudo C2-symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary.

Lewis acid-catalyzed Friedel-Crafts reactions toward highly versatile, α-quaternary oxime ethers

The synthesis of all-carbon-substituted, quaternary stereocenters through Lewis acid-catalyzed Friedel-Crafts alkylation of cyclic and acyclic 2-hydroxy oxime ethers proceeds under mild reaction conditions and with high yields. Moreover, the oxime ether m

METHODS OF PREPARING a,?-UNSATURATED OR a-HALO KETONES AND ALDEHYDES

Copper(II) bromide mediated oxidation of acylated enol and use of the reaction in the synthesis of α,β-unsaturated or α-bromo ketones or aldehydes are disclosed. The method provides an efficient and practical process for manufacturing dehydrohedione (DHH) and many other versatile α,β-unsaturated or α-bromo ketones or aldehydes in large scales to avoid using precious metal compounds.

Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C-F bond cleavage

The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C-F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditio

α,β-Unsaturated ketones via copper(II) bromide mediated oxidation

A protocol for effecting a rapid Saegusa-type oxidation of enol acetates is reported. This new method relies on the in situ elimination of an α-bromo intermediate to generate α,β-unsaturated ketones using copper(II) bromide. The methodology developed was applied to a range of substrates including a cyclohexanone, which could be directly converted to the corresponding phenol derivative. A catalytic system in which a non-masked ketone was successfully oxidised using substoichiometric CuBr2 was also developed as a proof of principle.

A simple primary amine catalyst for enantioselective α-hydroxylations and α-fluorinations of branched aldehydes

A new primary amine catalyst for the asymmetric α-hydroxylation and α-fluorination of α-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for α-functionalizations. Promising initial results in α-amination and α-chlorination reactions support this hypothesis.

Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones

The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me2Zn and aminoalcohol catalyst promoted the aldol addition/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92 %), high enantioselectivities (up to 96 %), and complete diastereoselectivity. The chiral oxazolines were then used to give, after a straightforward acid hydrolysis, enantioenriched building blocks bearing tertiary alcohol motifs such as hydroxylaldehydes, hydroxylacids, and hydroxylesters without racemization.

Highly efficient C-H hydroxylation of carbonyl compounds with oxygen under mild conditions

A transition-metal-free Cs2CO3-catalyzed α-hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α-hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very environmentally friendly and practical. This transformation is highly efficient and highly selective for tertiary C(sp3)-H bond cleavage. OH, so simple! A transition-metal-free Cs2CO 3-catalyzed α-hydroxylation of carbonyl compounds with O 2 provided a variety of tertiary α-hydroxycarbonyl compounds (see scheme; DMSO=dimethyl sulfoxide), which are widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very efficient and practical.

OXAZOLIDINONE COMPOUNDS AND DERIVATIVES THEREOF

Compounds of Formula (I) and Formula (II) are useful inhibitors of tankyrase. Compounds of Formula (I) and Formula (II) have the following structure: where the definitions of the variables are provided herein.

Alkyl 2-(2-benzothiazolylsulfinyl)acetates as useful synthetic reagents for alkyl 4-hydroxyalk-2-enoates by sulfinyl-Knoevenagel reaction

Isopropyl, ethyl, and methyl 2-(2-benzothiazolylsulfinyl)acetates have been found to be useful synthetic reagents for sulfinyl-Knoevenagel reaction with various aldehydes to give directly the corresponding 4-hydroxyalk-2-enoates [R′CH(OH)CHCHCO2R], which are ubiquitous structures in biologically active natural products and useful building blocks for organic synthesis of chiral compounds. From the optically pure (R)-2-(2- benzothiazolylsulfinyl)acetates (>99% ee) prepared by the enzymatic kinetic resolution of (±)-2-(2-benzothiazolylsulfinyl)acetates, optically active 4-hydroxyalk-2-enoates (up to 91% ee) have been obtained in good yields.