Asymmetric synthesis of γ-chiral borylalkanes via sequential reduction/hydroboration using a single copper catalyst. Issue 33 (17th August 2020)

• Record Type: Journal Article
• Authors: Han, Jung Tae; Lee, Jin Yong; Yun, Jaesook
• Is Part Of: Chemical science. Volume 11:Issue 33(2020)
• Page Start: 8961
• Page End: 8965
• Publication Date: 2020-08-17
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc03759a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Copper-catalyzed reductive hydroboration of γ, γ-disubstituted allylic substrates enables preparation of γ-chiral alkylboron compounds in a one-pot cascade manner. Abstract : The synthesis of γ-chiral borylalkanes through copper-catalyzed enantioselective SN 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.