1407797-82-3

Upstream product

• 862735-92-0 dimethyl(phenyl)(3-((tetrahydro-2H-pyran-2-yl)oxy)prop-1-yn-1-yl)silane 
• 862735-81-7 dimethyl-phenyl-[(Z)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-silane 
• 1407797-72-1 (Z)-1-dimethylphenysilyl-3-chloro-1-pentene 
• 126361-99-7 (Z)-3-(dimethyl-phenyl-silanyl)-prop-2-en-1-ol 
• 1350662-71-3 C₁₇H₃₁BO₂ 

Relevant academic research and scientific papers

Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes

Abstract We have presented full details of our work on alkylboranes, which we have introduced as new reagents for copper-catalyzed SN2′-type enantioselective allylic substitutions. The copper catalysis delivered enantioenriched chiral products containing tertiary or quaternary carbon stereogenic centers branched with functionalized sp3-alkyl groups. The wide availability of alkylboranes via the established alkene hydroboration reaction is an attractive feature of these transformations. Various functional groups are tolerated in the substrates. A reaction pathway involving addition-elimination of a neutral alkylcopper(I) species with the allyl chloride substrate is proposed.

Copper-catalyzed enantioselective allylic substitution with alkylboranes

The first catalytic enantioselective allylic substitution reaction with alkylboron compounds has been achieved. The reaction between alkyl-9-BBN reagents and primary allylic chlorides proceeded with excellent γ-selectivities and high enantioselectivities under catalysis of a Cu(I)-DTBM-SEGPHOS system. The protocol produces terminal alkenes with an allylic stereogenic center branched with functionalized sp3-alkyl groups. The reaction with a γ-silicon-substituted allyl chloride affords an efficient strategy for the enantioselective synthesis of functionalized α-stereogenic chiral allylsilanes.