1638110-81-2Relevant academic research and scientific papers
Construction of quaternary stereogenic carbon centers through copper-catalyzed enantioselective allylic cross-coupling with alkylboranes
Hojoh, Kentaro,Shido, Yoshinori,Ohmiya, Hirohisa,Sawamura, Masaya
supporting information, p. 4954 - 4958 (2014/05/20)
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.
