1638110-91-4

Upstream product

• 1334681-19-4 (E)-(5-chloro-3-methylpent-3-en-1-yl)benzene 
• 3277-89-2 phenethylmagnesium bromide 
• 72681-08-4 (E)-3-methyl-5-phenyl-pent-2-en-1-ol 
• 36805-43-3 ethyl (E)-3-methyl-5-phenylpent-2-enoate 
• 183440-00-8 triisopropyl(pent-4-en-1-yloxy)silane 
• 1258222-46-6 C₂₂H₄₅BOSi 

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.

Construction of quaternary stereogenic carbon centers through copper-catalyzed enantioselective allylic cross-coupling with alkylboranes

A combination of an in situ generated chiral CuI/DTBM-MeO-BIPHEP catalyst system and EtOK enabled the enantioselective SN2'-type allylic cross-coupling between alkylborane reagents and γ,γ- disubstituted primary allyl chlorides with enantiocontrol at a useful level. The reaction generates a stereogenic quaternary carbon center having three sp 3-alkyl groups and a vinyl group. This protocol allowed the use of terminal alkenes as nucleophile precursors, thus representing a formal reductive allylic cross-coupling of terminal alkenes. A reaction pathway involving addition/elimination of a neutral alkylcopper(I) species with the allyl chloride substrate is proposed.