111688-22-3

Upstream product

• 67-56-1 methanol 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 
• 17257-70-4 (R)-α-hydroxy-α-trifluoromethylphenyl acetic acid 
• 20698-90-2 (R)-3,3,3-Trifluoro-2-hydroxy-2-phenyl-propionic acid methyl ester 
• 74-88-4 methyl iodide 

Downstream Products

• 1097731-62-8 (2R)-2-methylhex-5-en-1-yl (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 
• 1360572-14-0 (2S)-2-methylhex-5-en-1-yl (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 
• 20445-31-2 R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid 

Relevant academic research and scientific papers

Molecular Mechanics Calculations and Comparison of Proton, Fluorine, and Carbon NMR Diastereomer Discrimination via Nonbonding Interactions between Fluorine-Labeled Enantiomeric Amides and Enantiomerically Pure Chiral Solvating Agents

Diastereomer discrimination of fluorine-labeled enantiomers in chloroform solutions was studied with and without two chiral solvating agents (1S and 2S) using 1H, 13C, and 19F NMR spectroscopy.Although by 13C NMR spectroscopy the diastereomer discrimination is not observable, changes of chemical shifts for some carbon atoms unambiguously show formation of nonbonding interactions between the enantiomers and the chiral solvating agents.The position and the ratio of signal sets in both hydrogen and fluorine NMR spectra correspond to the enantiomeric composition in the solution.On the basis of changes in the chemical shifts of enantiomers in chloroform solutions of chiral solvating agent, binding constants and binding energy differences were calculated.Using the MM2 force field, calculations were performed on binding complexes between the chiral solvating agent 2S and enantiomers 6.It was shown that demand for energy differences between diastereomeric nonbonding complexes of racemic amides and the chiral solvating amides necessary to obtain their NMR diastereomer discrimination is low for 1H, intermediary for 19F, and high for 13C NMR.

Chemoselective CaO-mediated acylation of alcohols and amines in 2-methyltetrahydrofuran

Calcium oxide is proposed as an innocuous acid scavenger for the chemoselective synthesis of amide- and ester-type compounds. Although these molecules have wide spread applications in organic and pharmaceutical chemistry, and a large number of routes have been designed for their synthesis, the development of more efficient and environmentally friendly acylation strategies remains an ongoing challenge. The use of CaO allows for the stoichiometric acylation of primary alcohols in the presence of phenols or tertiary alcohols; amines can also be subjected to acylation reactions in the presence of hydroxyl groups. Chirality is obtained through acylation if the starting material is an optically pure alcohol or if a chiral acylating agent is used. Furthermore, the use of 2-methyltetrahydrofuran (2-MeTHF), a more ecofriendly solvent, leads to maximized yields. This protocol is successfully applied to the synthesis of an interesting N-aryloxazolidin-2-one intermediate for the preparation of linezolid-type compounds.