Asymmetric synthesis of γ-chiral borylalkanes via sequential reduction/hydroboration using a single copper catalyst |
| |
Authors: | Jung Tae Han Jin Yong Lee Jaesook Yun |
| |
Institution: | Department of Chemistry, Institute of Basic Science, Sungkyunkwan University, Suwon 16419 Korea, |
| |
Abstract: | The synthesis of γ-chiral borylalkanes through copper-catalyzed enantioselective SN2′-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.Copper-catalyzed reductive hydroboration of γ,γ-disubstituted allylic substrates enables preparation of γ-chiral alkylboron compounds in a one-pot cascade manner. |
| |
Keywords: | |
|
|