161745-73-9

Upstream product

• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 220858-71-9 3-<7-chloro-3-(S)-hydroxy-2-(R)-phenylheptanoyl>-4-(R)-phenyl-2-oxazolidinone 
• 1335544-72-3 (4R)-4-phenyl-3-[(2R)-3,3,3-trifluoro-2-phenylpropanoyl]-1,3-oxazolidin-2-one 
• 21037-34-3 (2R₃R)-2,3-Diphenylbernsteinsaeure 
• 220858-72-0 3-<7-chloro-3-(S)-(methylsulfonyl)oxy-2-(R)-phenylheptanoyl>-4-(R)-phenyl-2-oxazolidinone 
• 220858-74-2 β-(R)-phenyl-1-(phenylmethyl)-2-(R)-piperidineethanol 
• 220858-77-5 (2R,3S)-7-Chloro-3-methanesulfonyloxy-2-phenyl-heptanoic acid methyl ester 
• 220858-73-1 α-(S)-(4-chlorobutyl)-β-(S)-(hydroxymethyl)benzeneethanol methanesulfonate 
• 220858-75-3 β-(R)-phenyl-2-(R)-piperidineethanol 
• 220858-76-4 1-(tert-butyloxycarbonyl)-α-(R)-phenyl-2-(R)-piperidineacetic acid 
• 203056-18-2 (1R)-1-[(2R)-N-(tert-butyloxycarbonyl)piperidin-2-yl]-1-phenyl-2-hydroxyethane 
• 19262-68-1 dexmethylphenidate hydrochloride 

Relevant academic research and scientific papers

Diastereoselective Electrophilic Trifluoromethylthiolation of Chiral Oxazolidinones: Access to Enantiopure α-SCF3 Alcohols

Lithium imide enolates featuring Evans’ chiral oxazolidinone auxiliary were involved in diastereoselective α-trifluoromethylthiolation with electrophilic SCF3 donors. Diastereopure products were isolated and converted to enantiopure α-SCF3 alcohols without racemisation. (Figure presented.).

Synthesis of α-CF3-substituted carbonyl compounds with relative and absolute stereocontrol using electrophilic CF3-transfer reagents

Evans-type chiral lithium imide enolates undergo diastereoselective α-trifluoromethylation with a hypervalent iodine-CF3 reagent with up to 91% combined isolated yield and 97:3 dr. The resulting isolated diastereopure products can be further transformed into valuable products without racemization.

Diastereoselective Electrochemical Carboxylation of Chiral α-Bromocarboxylic Acid Derivatives: An Easy Access to Unsymmetrical Alkylmalonic Ester Derivatives

The diastereoselective electrochemical carboxylation of chiral N-(2-bromoacyl)oxazolidin-2-ones has been studied. This reaction was carried out by cathodic reduction of the C - Br bond, in the presence of carbon dioxide, followed by treatment with diazomethane. The yields and the diastereomeric ratio of the two epimeric alkylmalonic acid derivatives are strongly affected by various factors: solvent-supporting electrolyte system, temperature, electrode material, electrolysis conditions, oxazolidinone moiety. The higher yields (88%) were obtained starting from N-(2-bromopropionyl)-4R-phenyloxazolidin-2-one la, but with poor diastereoselectivity (61:39). The two epimers were easily separated by flash chromatography. The best results were achieved using a different chiral auxiliary: Oppolzer's camphor sultam. Starting from 1j a good yield in carboxylated product was obtained (80%) with excellent diastereoselectivity (98:2). These chiral alkylmalonic acid derivatives are valuable building blocks in the synthesis of molecules with biological activity and of chiral propane-1,3-diols derivatives.

A convenient method for synthesis of optically active methylphenidate from N-methoxycarbonylpiperidine by utilizing electrochemical oxidation and Evans aldol-type reaction

A new method to prepare optically active methylphenidate starting from piperidine is described. The method consists of a transformation of N-methoxycarbonylated piperidine to the corresponding α-methoxylated carbamate utilizing electrochemical oxidation f

A convenient and practical method for N-acylation of 2 oxazolidinone chiral auxiliaries with acids

A one-pot, convenient and practical method for N-acylation of 2- oxazolidinone chiral auxiliaries directly with acids in the presence of pivaloyl chloride and triethylamine is described.

Asymmetric synthesis of optically active 2,3-diarylsuccinic acids by oxidative homocoupling of chiral 3-(arylacetyl)-2-oxazolidones

Oxidative homocoupling of chiral 3-(arylacetyl)-2-oxazolidones 1 was achieved by treatment with DABCO-TiCl4 or DMAP-TiCl4 and afforded the corresponding dimers stereospecifically. The reaction of (4S)- and (4R)-substituted 1 gave (S,S)- and (R,R)-dimers respectively. The obtained dimers were easily transformed to the corresponding 2,3-diaryl succinic acids. This reaction therefore provides a useful method For the synthesis of optically pure 2,3-diarylsuccinic acids. The oxidative coupling was not inhibited by para substitution of an electron donating group on the aryl group. A para-substituted electron withdrawing group and an ortho-substituent, however, hindered the coupling.