1101249-56-2

Upstream product

• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 794525-96-5 (S)-3-methyl-1-[2-(p-tolylsulfinyl)phenyl]butan-2-one 

Downstream Products

• 1393107-07-7 C₂₄H₂₆O₂S 
• 1378384-00-9 2-methyl-1-{(1S,2S,4S)-2-[2-((S)-p-tolylsulfinyl)phenyl]bicyclo[2.2.1]hept-5-en-2-yl}propan-1-one 

Relevant academic research and scientific papers

The sulfinyl group as a remote chiral auxiliary in stereoselective conjugate additions of alkyl groups to α-methylidene carbonyl compounds initiated by Et3B/O2

Reactions of α-[2-(p-tolylsulfinyl)phenyl] α-methylidene carbonyl compounds 1 and 2 with alkyl radicals generated from Et 3B/O2 and RI give, after protonation, β-alkyl derivatives with a high degree of control of the configuration at the α carbon. In the case of aldehyde 2, when further combined with allylation of the carbonyl group, a one-pot radical-addition/protonation/allylation sequence provides a highly stereoselective synthesis of compounds bearing two adjacent chiral centres. The stereochemical course of the reaction is controlled by the sulfinyl group acting as a remote chiral auxiliary, and this group can be easily removed with tBuLi. The sulfinyl group can be an efficient remote chiral auxiliary in the stereoselective radical addition to α-methylidene carbonyl compounds. Radicals were generated from alkyl iodides with Et 3B/O2. The stereocontrol comes from the formation of chelated complexes of the Lewis acid with the carbonyl and sulfinyl oxygen atoms. This process gives access to enantiopure compounds with chiral benzylic centres. Copyright

Remote stereocontrol mediated by a sulfinyl group: Synthesis of allylic alcohols via chemoselective and diastereoselective reduction of γ-methylene δ-ketosulfoxides

The efficiency of the sulfinyl group as a remote controller of the chemoselectivity and diastereoselectivity of the reduction of α,β-unsaturated α-[2-(p-tolylsulfinyl)phenyl] substituted ketones 1 has been demonstrated in reactions carried out under NaBH