Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes

Shengnan Jin, Jinxia Li, Kang Liu, Wei-Yi Ding, Shuai Wang, Xiujuan Huang, Xue Li, Peiyuan Yu () and Qiuling Song ()
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Shengnan Jin: Huaqiao University
Jinxia Li: Southern University of Science and Technology
Kang Liu: Huaqiao University
Wei-Yi Ding: Southern University of Science and Technology
Shuai Wang: Huaqiao University
Xiujuan Huang: Huaqiao University
Xue Li: Huaqiao University
Peiyuan Yu: Southern University of Science and Technology
Qiuling Song: Huaqiao University

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract Chiral organoborons are of great value in asymmetric synthesis, functional materials, and medicinal chemistry. The development of chiral bis(boryl) alkanes, especially optically enriched 1,1-diboron compounds, has been greatly inhibited by the lack of direct synthetic protocols. Therefore, it is very challenging to develop a simple and effective strategy to obtain chiral 1,1-diborylalkanes. Herein, we develop an enantioselective copper-catalyzed cascade double hydroboration of terminal alkynes and highly enantioenriched gem-diborylalkanes were readily obtained. Our strategy uses simple terminal alkynes and two different boranes to construct valuable chiral gem-bis(boryl) alkanes with one catalytic and one ligand pattern, which represents the simplest and most straightforward strategy for constructing such chiral gem-diborons.

Date: 2022
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DOI: 10.1038/s41467-022-31234-2

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