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.
Nature communications. 2021 Jun 18;12(1):3776. doi: 10.1038/s41467-021-24012-z Q115.72025
Enantioselective synthesis of tertiary boronic esters through catalytic asymmetric reversed hydroboration
催化不对称逆向硼化合成叔硼酸酯类化合物 翻译改进
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DOI: 10.1038/s41467-021-24012-z PMID: 34145273
摘要 Ai翻译
Keywords：tertiary boronic esters
关键词：催化不对称反向氢硼化; 三级硼酸酯
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