Enantioselective synthesis of tertiary boronic esters through catalytic asymmetric reversed hydroboration

Tao-Tao Gao, Hou-Xiang Lu, Peng-Chao Gao and Bi-Jie Li ()
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Tao-Tao Gao: Tsinghua University
Hou-Xiang Lu: Tsinghua University
Peng-Chao Gao: Tsinghua University
Bi-Jie Li: Tsinghua University

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Chiral tertiary boronic esters are important precursors to bioactive compounds and versatile synthetic intermediates to molecules containing quaternary stereocenters. The development of conjugate boryl addition to α,β-unsaturated amide has been hampered by the intrinsic low electrophilicity of the amide group. Here we show the catalytic asymmetric synthesis of enantioenriched tertiary boronic esters through hydroboration of β,β-disubstituted α,β-unsaturated amides. The Rh-catalyzed hydroboration occurs with previously unattainable selectivity to provide tertiary boronic esters in high enantioselectivity. This strategy opens a door for the hydroboration of inert Michael acceptors with high stereocontrol and may provide future applications in the synthesis of biologically active molecules.

Date: 2021
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-24012-z

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DOI: 10.1038/s41467-021-24012-z

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