126186-85-4

Upstream product

• 1015198-84-1 (R)-methyl 2-[(N-t-butylsulfinylimine)methyl]benzoate 
• 920-39-8 isopropylmagnesium bromide 
• 4122-56-9 methyl o-formylbenzoate 
• 146374-27-8 S-tert-butylsulfinimide 
• 1356832-81-9 3-hydroxy-3-isopropylisoindolin-1-one 

Relevant academic research and scientific papers

The Vibrational Circular Dichroism Pattern of the ν(C=O) Bands in Isoindolinones

The IR and vibrational circular dichroism (VCD) spectra of both enantiomers of Me-, iPr-, nBu-, Ph-, and CH2Ph-substituted isoindolinones in solution and KBr pellets were measured and interpreted by DFT calculations. The spectra in solution revealed no important differences in the C=O stretching vibration region while the interpretation of very distinct spectra taken in pellets required determining the crystal structures. The studied compounds crystallized in the P212121 (Me, iPr, CH2Ph), P31 (nBu), and P21 (Ph) space groups. We found that the quality of simulated spectra strongly depends on the substituent, the structure of the molecular cluster assumed, basis set, and use of the dispersion correction. The IR spectra can be reproduced well based on the simplest linear arrangement of hydrogen-bonded chains mimicking the molecular arrangement in the crystals. We found no common approach to reproduce all the registered VCD spectra in the crystal phase. For the Me and nBu isoindolinones, the VCD pattern was the best reproduced by full optimization of the selected large molecular clusters. For iPr, Ph and CH2Ph derivatives optimizing only the position of H-atoms in a fragment frozen as in the crystal provides the best results. Such an approach can reduce the computation time from months to one week.

Stereoselective synthesis of isoindolinones and tert-butyl sulfoxides

A reaction of Grignard reagents with an optically pure N-sulfinylimine derived from methyl 2-formylbenzoate yields enantioenriched isoindolinones and tert-butyl sulfoxides. The products are formed by the addition of the nucleophile to N-sulfinylimine followed by cyclization to form N-tert-butylsulfinylisoindolinone, which readily undergoes substitution with a second equivalent of Grignard reagent. The reaction can be carried out in dichloromethane at room temperature or at elevated temperatures without any loss of stereoselectivity. The use of nucleophiles other than Grignard reagents has also been investigated.

Synthesis of enantiomerically pure (α-phenylalkyl)amines with substituents at the ortho position through diastereoselective radical alkylation reaction of sulfinimines

The alkyl radical (R1) addition reaction to ortho-X-substituted N-(benzylidene)-2-methylpropane-2-sulfinamides (X = Br, CN, CO2Me, OH and OMe) is highly diastereoselective, regardless of the electronic properties of the X group and t

Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones

Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones, was developed using chiral phosphoric acid as catalyst and a Hantzsch ester as the hydrogen source with up to 95% ee. The reaction process of this asymmetric