Abstract
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 sp3-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.
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