170751-77-6

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 104871-67-2 (R)-2-(p-tolylsulfinyl)-1-cyclohexanone 
• 170751-79-8 (1S,2S,(S)R)-1-etinil-2-p-tolilsulfinilciclohexan-1-ol 

Relevant academic research and scientific papers

Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones

We describe the addition reactions of α-thiocarbanions derived from sulfoxides, thioethers, and sulfones to 2-(p-tolylsulfinyl)cyclohexanones. The high stereoselectivity observed in the formation of the chiral hydroxylic carbon is controlled by the configuration of the sulfinyl group at the substrate, but it is modulated by the nature of the sulfur function at the reagent (SOTol>SO2Ph>SPh). The highly stereoselective formation of the second stereogenic center generated in these reactions from prochiral anions is only achieved with sulfinylcarbanions, the configuration of which controls that of such a center. (C) 2000 Elsevier Science Ltd.

Estereoselectividad de la Adicion de Reactivos de Aluminio y de Magnesio a ((S)R)-2-p-Tolilsulfinilciclohexanonas

The results obtained in the reactions of ((S)R)-2-p-tolylsulfinyl cyclohexanones with several aluminum and magnesium reagents are reported.High diastereoselectivities are observed in the presence of ZnBr2 regardeless of the metal and the nature of the organic residue added (alkyl, aryl, vinyl or ethynyl).An efficient 1,3-asymmetric induction process controlled by the sulfoxide gives rise to tertiary alkylcarbinols with a defined configuration of the new stereogenic center.Key words: ketosulfoxides, nucleophilic addition, optically pure tertiary carbinols, aluminum and Grignard reagents.