Asymmetric synthesis of γ-chiral borylalkanes<i>via</i>sequential reduction/hydroboration using a single copper catalyst
Jung Tae Han, Jin Yong Lee, Jaesook Yun
Abstract
2'-reduction of γ,γ-disubstituted allylic substrates and subsequent hydroboration was reported. A copper-DTBM-Segphos catalyst produced a range of γ-chiral alkylboronates from easily accessible allylic acetate or benzoate with high enantioselectivities up to 99% ee. Furthermore, selective organic transformations of the resulting γ-chiral alkylboronates generated the corresponding γ-chiral alcohol, arene and amine compounds.
Topics & Concepts
HydroborationCascadeCopperAllylic rearrangementChemistryCatalysisReduction (mathematics)Combinatorial chemistryOrganic chemistryMathematicsChromatographyGeometryOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis