Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates

Yao Zhang, Deyong Qiao, Mei Duan, You Wang () and Shaolin Zhu ()
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Yao Zhang: Nanjing University
Deyong Qiao: Nanjing University
Mei Duan: Nanjing University
You Wang: Nanjing University
Shaolin Zhu: Nanjing University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Chiral α-aminoboronic acids and their derivatives are generally useful as bioactive compounds and some have been approved as therapeutic agents. Here we report a NiH-catalysed asymmetric hydroamidation process that with a simple amino alcohol ligand can easily produce a wide range of highly enantioenriched α-aminoboronates from alkenyl boronates and dioxazolones under mild conditions. The reaction is proposed to proceed by an enantioselective hydrometallation followed by an inner-sphere nitrenoid transfer and C–N bond forming sequence. The synthetic utility of this transformation was demonstrated by the efficient synthesis of a current pharmaceutical agent, Vaborbactam.

Date: 2022
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DOI: 10.1038/s41467-022-33411-9

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