302934-18-5

Upstream product

• 100-52-7 benzaldehyde 
• 302934-10-7 (S)-1-ethyl-2-(p-tolylsulfinyl)benzene 
• 1517-82-4 (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfinate 
• 1973-22-4 1-bromo-2-ethylbenzene 

Downstream Products

• 738617-37-3 (1S,2S,(S)S)-1-phenyl-2-[2-(p-tolylsulfinyl)phenyl]-1-trimethylsilyloxypropane 

Relevant academic research and scientific papers

About the stereoselectivity control in reactions of chiral ortho-sulfinyl benzyl carbanions with aldehydes

Reactions of aliphatic and aromatic aldehydes with the benzyllithium derived from 2-p-tolylsulfinyl ethylbenzene yield mixtures of mainly two compounds, anti-3 and syn-4, epimers at hydroxylic carbon, easily separated by chromatography and desulfinylated into enantiomerically pure 1-alkyl (or aryl)-2-phenyl-1-propanols. The observed stereoselectivity at C(1) and C(2) is analyzed to the light of the steric and electronic effects of the substituents.

Enantioselective generation of benzylic stereocenters mediated by a remote sulfoxide

Ortho-Sulfinyl-substituted benzyllithium reagents react with aldehydes and ketones to afford, after desulfurization with Raney-Nickel, stereoselective access to benzylic stereocenters [Eq. (1)]. This is the first efficient asymmetric 1,4-induction with mediation by a sulfoxide group. LDA = lithium diisopropylamide; Tol = tolyl; TIPS = triisopropylsilyl.