1407797-91-4Relevant academic research and scientific papers
Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes
Hojoh, Kentaro,Shido, Yoshinori,Nagao, Kazunori,Mori, Seiji,Ohmiya, Hirohisa,Sawamura, Masaya
, p. 6519 - 6533 (2015/08/18)
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
Shido, Yoshinori,Yoshida, Mika,Tanabe, Masahito,Ohmiya, Hirohisa,Sawamura, Masaya
, p. 18573 - 18576 (2013/01/15)
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.
