142697-15-2

Upstream product

• 142611-82-3 Acetic acid (S)-3-(dimethyl-phenyl-silanyl)-1-methyl-prop-2-ynyl ester 
• 142611-82-3 (R)-4-(dimethyl(phenyl)silyl)-but-3-yn-2-yl acetate 
• 263914-77-8 (R)-(Z)-3-[1-(dimethylphenylsilyl)-1-butenyl] acetate 
• 1378249-47-8 C₁₇H₂₄O₂Si 
• 142697-17-4 (S)-4-(dimethyl(phenyl)silyl)-but-3-yn-2-ol 
• 129921-47-7 Acetic acid (Z)-(S)-3-(dimethyl-phenyl-silanyl)-1-methyl-allyl ester 

Downstream Products

• 142611-72-1 (3S)-(Z)-1-(Dimethylphenylsilyl)-1-buten-3-yl (benzyloxy)acetate 
• 142611-71-0 (3S)-(Z)-1-(Dimethylphenylsilyl)-1-buten-3-yl methoxyacetate 
• 1378249-52-5 2-{[(2S,3Z)-4-[dimethyl(phenyl)silyl]-3-buten-2-yl]oxy}-5,5-dimethyl-1,3,2-dioxaphosphinane-2-oxide 
• 142611-68-5 (3R)-(Z)-1-(Dimethylphenylsilyl)-1-buten-3-yl (benzyloxy)acetate 
• 142611-69-6 (3R)-(Z)-1-(Dimethylphenylsilyl)-1-buten-3-yl ((4-methoxybenzyl)oxy)acetate 
• 142611-70-9 (3R)-(Z)-1-(Dimethylphenylsilyl)-1-buten-3-yl (methoxymethoxy)acetate 
• 142611-67-4 (3R)-(Z)-1-(Dimethylphenylsilyl)-1-buten-3-yl methoxyacetate 
• 142611-79-8 (2S,3R)-(E)-Methyl 2-(benzyloxy)-3-(dimethylphenylsilyl)hex-4-enoate 
• 142611-86-7 (2S,3R)-(E)-2-(Benzyloxy)-3-(dimethylphenylsilyl)hex-4-enoic acid 
• 142611-78-7 (2S,3R)-(E)-Methyl 2-methoxy-3-(dimethylphenylsilyl)hex-4-enoate 
• 133323-22-5 (E)-(2S,3R)-3-(Dimethyl-phenyl-silanyl)-2-methoxy-hex-4-enoic acid 
• 142611-75-4 (2S,3R)-(E)-Methyl 2-((4-methoxybenzyl)oxy)-3-(dimethylphenylsilyl)hex-4-enoate 
• 142611-84-5 (E)-(2S,3R)-3-(Dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-hex-4-enoic acid 
• 142611-76-5 (2S,3R)-(E)-Methyl 2-(methoxymethoxy)-3-(dimethylphenylsilyl)hex-4-enoate 

Relevant academic research and scientific papers

Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes

The scope of the copper-catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete γ-E-selectivity and preferential 1,3-syn stereoselectivity. The reaction of γ-silicon-substituted allylic phosphates affords enantioenriched α-stereogenic allylsilanes.

Reversible 1,3-anti/syn-stereochemical courses in copper-catalyzed γ-selective allyl-alkyl coupling between chiral allylic phosphates and alkylboranes

The stereochemical courses of the copper-catalyzed allyl-alkyl coupling between enantioenriched chiral allylic phosphates and alkylboranes were switchable between 1,3-anti and 1,3-syn selectivities by the choice of solvents and achiral alkoxide bases with different steric demands. The reactions with γ-silylated allylic phosphates allow efficient synthesis of enantioenriched chiral allylsilanes with tertiary or quaternary carbon stereogenic centers. Cyclic and acyclic bimodal participation of alkoxyborane species in an organocopper addition-elimination sequence is proposed to account for the phenomenon of the anti/syn-stereochemical reversal.

Stereoselective synthesis of (Z)- and (E)-allylic silanes by copper- mediated substitution reactions of allylic carbamates with grignard reagents

Both (Z)- and (E)-allylic silanes were prepared with high stereoselectivity by the copper-mediated substitution of allylic carbamates by organometallic reagents. The reaction of alkylmagnesium reagents with (E)- allylic carbamates provides (Z)-allylic silanes, whereas both alkylmagnesium and alkyllithium reagents react with (Z)-allylic carbamates to afford (E)- allylic silanes. Because Grignard reagents are often more facile to prepare than alkyllithium species, these reagents are the optimal nucleophiles for the synthesis of both (Z)- and (E)-allylic silanes. This method also allows readily available nonracemic allylic carbamates to be converted to chiral, nonracemic (Z)- and (E)-allylic silanes with high stereoselectivity.