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Copper-catalyzed enantioselective allylic substitution with alkylboranes
Yoshinori Shido1, Mika Yoshida, Masahito Tanabe
1Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Japan.
Abstract:
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 sp(3)-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.
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