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. 2020 Aug 6;11(33):8961-8965.
doi: 10.1039/d0sc03759a.

Asymmetric synthesis of γ-chiral borylalkanes via sequential reduction/hydroboration using a single copper catalyst

Jung Tae Han  1 , Jin Yong Lee  1 , Jaesook Yun  1
Affiliations

Asymmetric synthesis of γ-chiral borylalkanes via sequential reduction/hydroboration using a single copper catalyst

Jung Tae Han et al. Chem Sci. .

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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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Representative functionalized γ-chiral compounds.
Scheme 1
Scheme 1. Approaches to γ-chiral organoboron compounds.
Fig. 2
Fig. 2. Structures of the chiral ligands.
Scheme 2
Scheme 2. Mechanistic studies.
Fig. 3
Fig. 3. Proposed mechanism of copper-catalyzed reductive hydroboration.
Scheme 3
Scheme 3. Application of γ-chiral alkylboron compounds.
See this image and copyright information in PMC

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