75593-30-5

Upstream product

• 73162-51-3 Acetic acid 1-methyl-1-phenylsulfanylmethyl-allyl ester 
• 100-39-0 benzyl bromide 
• 693-03-8 n-butyl magnesium bromide 
• 98713-50-9 2-methyl-4-phenyl-3-phenylthiobut-1-ene 
• 103697-38-7 2-acetoxy-2-methyl-1-phenylsulfinylbut-3-ene 
• 75593-22-5 2-methyl-4-phenyl-3-(phenylsulfonyl)-1-butene 
• 75593-21-4 2-methyl-3-phenylsulphinyl-4-phenylbut-1-ene 
• 103697-41-2 2-methyl-4-phenyl-1-phenylsulfinylbut-2-ene 

Relevant academic research and scientific papers

Stereoselective synthesis of trisubstituted olefins by a directed allylic substitution strategy

New methodology for the stereoselective synthesis of trisubstituted olefins is presented. The use of ortho-diphenylphosphanyl benzoate (o-DPPB) as a directing leaving group for copper-mediated allylic substitution with Grignard reagents allowed for the stereoselective construction of a wide range of E olefins, without the need for an adjacent electron-withdrawing group. Our modular three-step approach toward trisubstituted alkenes commenced with geminal α-methylene aldehydes. Addition of an organometallic reagent and introduction of the o-DPPB group by esterification was followed by the o-DPPB-directed copper-mediated allylic substitution with a Grignard reagent to furnish stereodefined trisubstituted olefins. Additionally, incorporation of a stereocenter from the chiral pool allowed the preparation of an enantiomerically pure olefin that bore three alkyl substituents in high E/Z selectivity.

Regio- and Stero-selective Desulphurizative γ-Substitution of α-Substituted β-Methylallyl Sulphoxides and Sulphones with Lithium Dialkylcuprates providing Trisubstituted Olefins

α-Substituted β-methylallyl sulphoxides (2) and sulphones (3) undergo regio- and stereo-selective desulphurizative γ-substitution by the action of lithium dialkylcuprates in ether.The reaction provides a new method for the synthesis of trisubstituted E-ol