234436-57-8

Upstream product

• 598-19-6 2-bromoallyl alcohol 
• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 

Downstream Products

• 234436-59-0 (-)-(S_S,6R)-3-(p-Tolylsulfinyl)-1,7-dioxaspiro<5.5>undec-2-ene 
• 261900-93-0 (S_S)-(+)-3-chloro-2-(p-tolylsulfinyl)prop-2-ene 
• 261900-96-3 (R)-1-Phenyl-3-((R)-toluene-4-sulfinyl)-but-3-en-1-ol 
• 371764-84-0 (R)-1-Pyridin-3-yl-3-((R)-toluene-4-sulfinyl)-but-3-en-1-ol 
• 439077-54-0 Methanesulfonic acid 2-((S)-toluene-4-sulfinyl)-allyl ester 
• 371764-92-0 (R)-4-Methylamino-1-pyridin-3-yl-3-((R)-toluene-4-sulfinyl)-butan-1-ol 
• 371764-94-2 3-[(S)-1-Methyl-4-((R)-toluene-4-sulfinyl)-pyrrolidin-2-yl]-pyridine 
• 261900-97-4 (R)-1-Cyclohexyl-3-((R)-toluene-4-sulfinyl)-but-3-en-1-ol 

Relevant academic research and scientific papers

Studies on the diastereoselective allylation of aldehydes with enantiopure 2-sulfinylallyl building blocks

A comparative study on the allylation of aldehydes with enantiopure (SS)-2-(p-tolylsulfonyl)-prop-2-en-1-ol (SS)-1a and the corresponding chloride (SS)-1b under two different reaction systems is reported. In general, better yields were obtained from chloride (SS)-1b, whereas higher diastereoinduction was observed from alcohol (SS)-1a. The sense of diastereoinduction is the same in both systems and the stereochemistry of the major diastereomer has been determined. Moreover, the configurational stability of the sulfoxide group on the resulting sulfinyl homoallylic alcohols 3 has been proven in each reaction system, which demonstrates the efficiency of the sulfoxide group as chiral auxiliary in these allylation processes. Finally, as an example of the synthetic potential of the resulting adducts, a total synthesis of natural enantioenriched (S)-nicotine from sulfinylalcohol 3h is reported.

Syntheses of both enantiomers of 1,7-dioxaspiro[5.5]undecane: Pheromone components of the olive fruit-fly Dacus oleae from a new chiral intermediate, the (S(s))-2-(p-tolylsulfinyl)prop-2-en-1-ol

Both enantiomers of 1,7-dioxaspiro[5.5]undecane, the pheromone components of the olive fruit-fly Dacus oleae have been synthesized from a new chiral sulfoxide, (Ss)-2-(p-tolylsulfinyl)prop-2-en-1-ol via hetero Diels-Alder reaction, chromatographic separation of the diastereomers on a silica gel column and desulfurization over Raney nickel as key steps.