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Asymmetric synthesis of γ-chiral borylalkanes via sequential reduction/hydroboration using a single copper catalyst
Jung Tae Han1, Jin Yong Lee1, Jaesook Yun1
1Department of Chemistry, Institute of Basic Science, Sungkyunkwan University Suwon 16419 Korea jaesook@skku.edu.
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.
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