198342-81-3

Upstream product

• 60199-16-8 (1,3,5-triisopropyl)benzenesulfinic acid sodium salt 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 717-74-8 1,3,5-triisopropyl benzene 

Downstream Products

• 198342-53-9 6-((S)-2,4,6-Triisopropyl-benzenesulfinyl)-1,4-dioxa-spiro[4.4]non-6-ene 

Relevant academic research and scientific papers

An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine

An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-D-glucose or l-menthol in the presence of triethylamine was treated with triphenylphos

Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones

The diastereoselectivity of intermolecular β-addition of alkyl radicals to 2-(arylsulfinyl)-2-cycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of 2-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the 1H NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the β-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.